A Route to Carbasugar Analogues - Jonathan Clayden - The ...

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_refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(13) _chemical_absolute_configuration syn _refine_ls_number_reflns 2509 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.74597(16) 1.07720(12) 0.59978(5) 0.0224(3) Uani 1 1 d . . . O2 O 0.85316(16) 1.21137(12) 0.80110(5) 0.0207(3) Uani 1 1 d . . . N1 N 0.55197(18) 0.93270(14) 0.61905(6) 0.0183(3) Uani 1 1 d . . . C1 C 0.6322(2) 1.02851(17) 0.63416(7) 0.0195(4) Uani 1 1 d . . . C2 C 0.6042(2) 0.90213(16) 0.56341(7) 0.0177(4) Uani 1 1 d . . . H2 H 0.5123 0.9197 0.5380 0.021 Uiso 1 1 calc R . . C3 C 0.7436(2) 0.99817(16) 0.55146(7) 0.0180(4) Uani 1 1 d . . . H3 H 0.8490 0.9522 0.5481 0.022 Uiso 1 1 calc R . . C4 C 0.6086(2) 1.10139(17) 0.68643(7) 0.0182(4) Uani 1 1 d . . . C5 C 0.7666(2) 1.10303(16) 0.72129(7) 0.0166(3) Uani 1 1 d . . . H5 H 0.8392 1.1682 0.7049 0.020 Uiso 1 1 calc R . . C6 C 0.7256(2) 1.14878(15) 0.77815(7) 0.0175(4) Uani 1 1 d . . . C7 C 0.5818(2) 1.12851(17) 0.80158(7) 0.0194(4) Uani 1 1 d . . . H7 H 0.5631 1.1548 0.8379 0.023 Uiso 1 1 calc R . . C8 C 0.4539(2) 1.06579(17) 0.77093(7) 0.0208(4) Uani 1 1 d . . . H8 H 0.3602 1.0365 0.7895 0.025 Uiso 1 1 calc R . . C9 C 0.4653(2) 1.04862(17) 0.71759(7) 0.0205(4) Uani 1 1 d . . . H9 H 0.3832 1.0031 0.6989 0.025 Uiso 1 1 calc R . . C10 C 0.5667(3) 1.23878(18) 0.67028(7) 0.0254(4) Uani 1 1 d . . . H10A H 0.4680 1.2393 0.6481 0.038 Uiso 1 1 calc R . . H10B H 0.6566 1.2749 0.6494 0.038 Uiso 1 1 calc R . . H10C H 0.5489 1.2891 0.7031 0.038 Uiso 1 1 calc R . . C11 C 0.8641(2) 0.97756(16) 0.72155(7) 0.0183(4) Uani 1 1 d . . . 299
H11 H 0.8924 0.9592 0.6829 0.022 Uiso 1 1 calc R . . C12 C 0.7710(2) 0.86323(16) 0.74238(7) 0.0208(4) Uani 1 1 d . . . H12A H 0.7395 0.8772 0.7803 0.031 Uiso 1 1 calc R . . H12B H 0.8401 0.7883 0.7400 0.031 Uiso 1 1 calc R . . H12C H 0.6736 0.8507 0.7202 0.031 Uiso 1 1 calc R . . C13 C 1.0248(2) 0.99158(18) 0.75205(9) 0.0267(4) Uani 1 1 d . . . H13A H 1.0905 0.9156 0.7468 0.040 Uiso 1 1 calc R . . H13B H 1.0032 1.0032 0.7909 0.040 Uiso 1 1 calc R . . H13C H 1.0837 1.0650 0.7381 0.040 Uiso 1 1 calc R . . C14 C 0.8279(2) 1.25963(18) 0.85485(7) 0.0229(4) Uani 1 1 d . . . H14A H 0.8102 1.1894 0.8800 0.034 Uiso 1 1 calc R . . H14B H 0.7327 1.3149 0.8550 0.034 Uiso 1 1 calc R . . H14C H 0.9236 1.3076 0.8663 0.034 Uiso 1 1 calc R . . C15 C 0.6557(2) 0.76646(16) 0.55634(7) 0.0183(4) Uani 1 1 d . . . C16 C 0.7354(2) 0.70087(18) 0.59737(7) 0.0229(4) Uani 1 1 d . . . H16 H 0.7541 0.7404 0.6314 0.028 Uiso 1 1 calc R . . C17 C 0.7879(3) 0.57792(19) 0.58883(8) 0.0281(4) Uani 1 1 d . . . H17 H 0.8419 0.5337 0.6171 0.034 Uiso 1 1 calc R . . C18 C 0.7618(3) 0.51959(18) 0.53929(9) 0.0292(4) Uani 1 1 d . . . H18 H 0.7974 0.4355 0.5336 0.035 Uiso 1 1 calc R . . C19 C 0.6835(2) 0.58456(19) 0.49813(8) 0.0276(4) Uani 1 1 d . . . H19 H 0.6666 0.5452 0.4639 0.033 Uiso 1 1 calc R . . C20 C 0.6296(2) 0.70694(18) 0.50665(7) 0.0231(4) Uani 1 1 d . . . H20 H 0.5746 0.7504 0.4784 0.028 Uiso 1 1 calc R . . C21 C 0.7137(2) 1.07484(16) 0.50097(7) 0.0180(4) Uani 1 1 d . . . C22 C 0.7765(2) 1.03311(17) 0.45186(7) 0.0230(4) Uani 1 1 d . . . H22 H 0.8464 0.9620 0.4512 0.028 Uiso 1 1 calc R . . C23 C 0.7381(3) 1.09433(18) 0.40382(7) 0.0272(4) Uani 1 1 d . . . H23 H 0.7804 1.0643 0.3703 0.033 Uiso 1 1 calc R . . C24 C 0.6379(3) 1.19955(19) 0.40461(7) 0.0280(4) Uani 1 1 d . . . H24 H 0.6108 1.2415 0.3717 0.034 Uiso 1 1 calc R . . C25 C 0.5778(3) 1.24278(18) 0.45361(8) 0.0274(4) Uani 1 1 d . . . H25 H 0.5107 1.3156 0.4543 0.033 Uiso 1 1 calc R . . C26 C 0.6143(2) 1.18102(17) 0.50177(7) 0.0229(4) Uani 1 1 d . . . H26 H 0.5716 1.2111 0.5352 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 300
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Dearomatising Addition of Organolit
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2.3 Synthetic Scope 64 2.3.1 Organo
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Abstract Dearomatising Addition of
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The Author The Author graduated fro
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Abbreviations & Conventions Ac acet
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RDS rate determining step R f RC rt
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Chapter 1: Introduction Chapter 1 -
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Chapter 1: Introduction controlled
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Chapter 1: Introduction diastereome
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Chapter 1: Introduction combine mor
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Chapter 1: Introduction O Ar Cl TMP
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Chapter 1: Introduction conditions,
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Chapter 1: Introduction chiral oxaz
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Chapter 1: Introduction Again a lar
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Chapter 1: Introduction 34 Scheme 1
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Chapter 1: Introduction The amino a
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Chapter 1: Introduction It was envi
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Chapter 1: Introduction COR' i) ATP
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Chapter 1: Introduction O i) ATPH,
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Chapter 1: Introduction 1.4 Nucleop
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Chapter 1: Introduction Unlike the
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Chapter 1: Introduction Diene (-)-8
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Chapter 1: Introduction A scheme su
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Chapter 1: Introduction Cl R + 93 S
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Chapter 2 - Dearomatising additions
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3.1 - Oxazoline synthesis 3.1.1.a H
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3.1 - Oxazoline synthesis O Ar OH i
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3.1 - Oxazoline synthesis 3.1.2 Gen
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3.1 - Oxazoline synthesis mCPBA O N
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3.1 - Oxazoline synthesis 3.1.4.b M
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3.1 - Oxazoline synthesis Ph Ph Ph
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3.2 - Oxazoline removal O N O OH 3N
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3.2 - Oxazoline removal O Me O N OM
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3.2 - Oxazoline removal However, th
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3.2 - Oxazoline removal 3.2.3 Reduc
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3.2 - Oxazoline removal Ph O N Ph P
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3.2 - Oxazoline removal 3.2.3.c Ami
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3.2 - Oxazoline removal Ph Ph Ph Ph
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3.2 - Oxazoline removal 3.2.5.b N-A
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3.2 - Oxazoline removal Ph Ph O N H
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3.2 - Oxazoline removal Ph Me Ph Me
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3.2 - Oxazoline removal 3.2.6 Deter
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Better, however, would be a method
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4.1 - Introduction HO OH OH HO OH O
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4.1 - Introduction (-)-Shikimic aci
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4.1 - Introduction followed by Flem
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4.2 - Carbasugar synthesis 4.2 Synt
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4.2 - Carbasugar synthesis stereoce
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4.2 - Carbasugar synthesis of the o
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4.2 - Carbasugar synthesis support
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4.2 - Carbasugar synthesis Ox* Ox*
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4.2 - Carbasugar synthesis OsO 4 (c
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4.2 - Carbasugar synthesis taken on
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4.2 - Carbasugar synthesis As well
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4.4 - Revised altrose synthesis 4.4
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4.4 - Revised altrose synthesis suf
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4.4 - Revised altrose synthesis ind
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4.5 - Mannose synthesis 4.5 Synthes
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4.5 - Mannose synthesis It is clear
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4.5 - Mannose synthesis considering
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4.5 - Mannose synthesis which would
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4.5 - Mannose synthesis One clear a
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4.5 - Mannose synthesis 4.5.2.b Epo
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4.5 - Mannose synthesis hydrolysis
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4.5 - Mannose synthesis The second
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4.6 - Summary 4.6 Summary & Future
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4.6 - Summary OH CDI, NH 2 OH.HCl,
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184
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References (37) Rawson, D. J.; Meye
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References (105) Gajewski, J. J.; B
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References (169) McCormick, J. P.;
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References 192
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Experimental section 254nm, dodecam
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Experimental section General Proced
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Experimental for chapter 2 Synthesi
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Experimental for chapter 2 (CDCl 3
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Experimental for chapter 2 3H, OMe
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Experimental for chapter 2 Ph), 139
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Experimental for chapter 2 H4), 5.2
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Experimental for chapter 2 108 R f
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Experimental for chapter 2 Synthesi
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Experimental for chapter 3.1 satura
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Experimental for chapter 3.1 Na 2 S
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Experimental for chapter 3.1 Synthe
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Experimental for chapter 3.1 128.9,
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Experimental for chapter 3.1 Microw
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Experimental for chapter 3.1 R f :
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Page 247 and 248: Experimental for chapter 4.1 281 R
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Page 269 and 270: Experimental for chapter 4.2 cm 3 )
Page 273 and 274: Experimental for chapter 4.2 5.7 Re
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Page 285 and 286: Absolute structure parameter 1.3(11
Page 287 and 288: _diffrn_standards_interval_time ? _
Page 289 and 290: H13 H 0.8405 0.7136 -0.0889 0.026 U
Page 291 and 292: C4 C5 1.454(2) . ? C5 C6 1.324(2) .
Page 293 and 294: C24 C23 C22 120.0(2) . . ? C24 C23
Page 295 and 296: . Compound 102c Ph O N Ph Me 102c O
Page 297: _diffrn_standards_interval_time ? _
Page 301 and 302: C2 H2 1.0000 . ? C3 C21 1.506(2) .
Page 303 and 304: C26 C21 C3 121.41(15) . . ? C23 C22
Page 305 and 306: c. Compound 213 Ph O N Ph Me OH 213
Page 307 and 308: _cell_volume 1080.9(4) _cell_formul
Page 309 and 310: _refine_ls_number_reflns 4736 _refi
Page 311 and 312: H25 H 0.7979 0.2335 0.3365 0.028 Ui
Page 313 and 314: C4 0.025(4) 0.019(4) 0.018(4) 0.001
Page 315 and 316: loop_ _geom_bond_atom_site_label_1
Page 317 and 318: C9 C4 C1 107.1(5) . . ? C10 C4 C1 1
Page 319 and 320: C36 C38 H38A 109.5 . . ? C36 C38 H3
Page 321 and 322: C29 C30 C36 C37 -90.4(7) . . . . ?
Page 323 and 324: The structure was solved by the dir
Page 325 and 326: _reflns_number_total 2447 _reflns_n
Page 327 and 328: C7 C 1.1671(4) 0.7629(7) 1.2254(4)
Page 329 and 330: C3 0.015(3) 0.016(3) 0.021(3) -0.00
Page 331 and 332: C21 H21A 0.9800 . ? C21 H21B 0.9800
Page 333 and 334: H21A C21 H21C 109.5 . . ? H21B C21
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