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

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_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 C1 C 0.83045(16) 0.49054(15) 0.14451(14) 0.0204(5) Uani 1 1 d . . . C2 C 0.92740(14) 0.41706(15) 0.17390(14) 0.0207(5) Uani 1 1 d . . . H2 H 0.9720 0.4561 0.2236 0.025 Uiso 1 1 calc R . . C3 C 0.88510(15) 0.32101(14) 0.22610(14) 0.0220(5) Uani 1 1 d . . . H3 H 0.9308 0.2867 0.2727 0.026 Uiso 1 1 calc R . . C4 C 0.78501(16) 0.28394(15) 0.20775(14) 0.0200(5) Uani 1 1 d . . . C5 C 0.71032(15) 0.33576(15) 0.13987(14) 0.0233(5) Uani 1 1 d . . . H5 H 0.6448 0.3015 0.1194 0.028 Uiso 1 1 calc R . . C6 C 0.73267(15) 0.43020(16) 0.10625(14) 0.0236(5) Uani 1 1 d . . . H6 H 0.6866 0.4604 0.0574 0.028 Uiso 1 1 calc R . . C7 C 0.79109(16) 0.55021(14) 0.23711(14) 0.0300(6) Uani 1 1 d . . . H7A H 0.8506 0.5951 0.2611 0.045 Uiso 1 1 calc R . . H7B H 0.7708 0.5004 0.2887 0.045 Uiso 1 1 calc R . . H7C H 0.7269 0.5929 0.2202 0.045 Uiso 1 1 calc R . . C8 C 1.00781(15) 0.38867(16) 0.08889(14) 0.0242(5) Uani 1 1 d . . . H8 H 1.0342 0.4554 0.0592 0.029 Uiso 1 1 calc R . . C9 C 0.95494(15) 0.32482(14) 0.00635(15) 0.0298(6) Uani 1 1 d . . . H9A H 0.9297 0.2580 0.0328 0.045 Uiso 1 1 calc R . . H9B H 1.0092 0.3125 -0.0459 0.045 Uiso 1 1 calc R . . H9C H 0.8920 0.3630 -0.0208 0.045 Uiso 1 1 calc R . . C10 C 1.10924(15) 0.33115(15) 0.12915(14) 0.0341(6) Uani 1 1 d . . . H10A H 1.0870 0.2626 0.1538 0.051 Uiso 1 1 calc R . . H10B H 1.1419 0.3716 0.1830 0.051 Uiso 1 1 calc R . . H10C H 1.1635 0.3225 0.0763 0.051 Uiso 1 1 calc R . . C11 C 0.80696(15) 0.13795(15) 0.31431(14) 0.0286(6) Uani 1 1 d . . . H11A H 0.8747 0.1166 0.2807 0.043 Uiso 1 1 calc R . . H11B H 0.7674 0.0761 0.3374 0.043 Uiso 1 1 calc R . . H11C H 0.8255 0.1822 0.3707 0.043 Uiso 1 1 calc R . . C12 C 0.86735(15) 0.56876(16) 0.06908(15) 0.0211(5) Uani 1 1 d . . . C13 C 0.89699(15) 0.66286(15) -0.06504(13) 0.0215(5) Uani 1 1 d . . . 289
H13 H 0.8405 0.7136 -0.0889 0.026 Uiso 1 1 calc R . . C14 C 0.96120(16) 0.71333(15) 0.02178(14) 0.0212(5) Uani 1 1 d . . . H14 H 1.0419 0.7126 0.0069 0.025 Uiso 1 1 calc R . . C15 C 0.97123(15) 0.63387(16) -0.15098(14) 0.0198(5) Uani 1 1 d . . . C16 C 0.97990(16) 0.53350(16) -0.18628(14) 0.0240(5) Uani 1 1 d . . . H16 H 0.9404 0.4786 -0.1555 0.029 Uiso 1 1 calc R . . C17 C 1.04686(16) 0.51316(16) -0.26732(15) 0.0291(5) Uani 1 1 d . . . H17 H 1.0531 0.4439 -0.2911 0.035 Uiso 1 1 calc R . . C18 C 1.10389(15) 0.59113(17) -0.31340(15) 0.0269(5) Uani 1 1 d . . . H18 H 1.1475 0.5763 -0.3699 0.032 Uiso 1 1 calc R . . C19 C 1.09767(16) 0.69211(16) -0.27715(15) 0.0278(5) Uani 1 1 d . . . H19 H 1.1388 0.7465 -0.3072 0.033 Uiso 1 1 calc R . . C20 C 1.03127(16) 0.71245(16) -0.19718(15) 0.0259(5) Uani 1 1 d . . . H20 H 1.0262 0.7816 -0.1729 0.031 Uiso 1 1 calc R . . C21 C 0.92576(16) 0.82249(16) 0.04727(13) 0.0210(5) Uani 1 1 d . . . C22 C 0.99991(16) 0.90429(16) 0.04092(13) 0.0253(5) Uani 1 1 d . . . H22 H 1.0746 0.8911 0.0241 0.030 Uiso 1 1 calc R . . C23 C 0.96523(19) 1.00542(17) 0.05915(14) 0.0325(6) Uani 1 1 d . . . H23 H 1.0161 1.0614 0.0544 0.039 Uiso 1 1 calc R . . C24 C 0.85718(19) 1.02462(16) 0.08415(14) 0.0334(6) Uani 1 1 d . . . H24 H 0.8334 1.0940 0.0959 0.040 Uiso 1 1 calc R . . C25 C 0.78323(18) 0.94337(16) 0.09222(15) 0.0321(6) Uani 1 1 d . . . H25 H 0.7089 0.9567 0.1103 0.039 Uiso 1 1 calc R . . C26 C 0.81767(16) 0.84271(16) 0.07395(15) 0.0271(5) Uani 1 1 d . . . H26 H 0.7668 0.7869 0.0797 0.033 Uiso 1 1 calc R . . N1 N 0.83959(12) 0.57312(12) -0.02097(12) 0.0220(4) Uani 1 1 d . . . O1 O 0.73859(10) 0.19485(10) 0.24714(9) 0.0239(3) Uani 1 1 d . . . O2 O 0.93834(10) 0.64334(10) 0.10419(10) 0.0244(4) Uani 1 1 d . . . 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 _atom_site_aniso_U_12 C1 0.0205(11) 0.0166(12) 0.0239(12) -0.0021(10) - 0.0007(10) 0.0000(10) C2 0.0209(12) 0.0197(13) 0.0214(12) -0.0001(10) - 0.0059(9) -0.0029(11) C3 0.0261(13) 0.0188(12) 0.0210(12) 0.0008(10) - 0.0036(9) 0.0032(10) C4 0.0228(12) 0.0145(12) 0.0228(12) 0.0003(10) 0.0009(10) 0.0007(10) C5 0.0181(11) 0.0252(14) 0.0265(13) -0.0045(11) - 0.0023(10) -0.0039(11) C6 0.0210(11) 0.0244(13) 0.0254(12) -0.0003(11) - 0.0048(10) 0.0029(10) 290
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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 237 and 238: Experimental for chapter 3.2 Synthe
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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: _diffrn_standards_interval_time ? _
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 and 298: _diffrn_standards_interval_time ? _
Page 299 and 300: H11 H 0.8924 0.9592 0.6829 0.022 Ui
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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