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

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C21 C22 C23 C24 0.4(3) . . . . ? C22 C23 C24 C25 0.7(3) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C24 C25 C26 C21 -0.2(3) . . . . ? C22 C21 C26 C25 1.3(3) . . . . ? C14 C21 C26 C25 -176.48(19) . . . . ? O2 C12 N1 C13 0.7(2) . . . . ? C1 C12 N1 C13 -179.88(18) . . . . ? C15 C13 N1 C12 121.00(17) . . . . ? C14 C13 N1 C12 -2.4(2) . . . . ? C3 C4 O1 C11 -0.1(3) . . . . ? C5 C4 O1 C11 179.39(15) . . . . ? N1 C12 O2 C14 1.5(2) . . . . ? C1 C12 O2 C14 -178.00(15) . . . . ? C21 C14 O2 C12 120.13(17) . . . . ? C13 C14 O2 C12 -2.78(18) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.175 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.035 295
. Compound 102c Ph O N Ph Me 102c OMe Identification code s2291abs Empirical formula C26 H29 N O2 Formula weight 387.50 Temperature 100(2) K Wavelength 0.71073 A Crystal system, space group Orthorhombic, P2(1)2(1)2(1) Unit cell dimensions a = 8.2463(6) A alpha = 90 deg. b = 10.6095(7) A beta = 90 deg. c = 24.6291(19) A gamma = 90 deg. Volume 2154.8(3) A^3 Z, Calculated density 4, 1.194 Mg/m^3 Absorption coefficient 0.075 mm^-1 F(000) 832 Crystal size 0.70 x 0.50 x 0.50 mm <strong>The</strong>ta range for data collection 1.65 <strong>to</strong> 26.37 deg. Limiting indices -10
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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 243 and 244: Experimental for chapter 3.2 Synthe
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: C24 C23 C22 120.0(2) . . ? C24 C23
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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