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

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C42 0.072(7) 0.028(5) 0.057(6) 0.013(5) -0.011(5) 0.009(5) C43 0.071(7) 0.010(4) 0.050(6) 0.002(4) 0.001(5) 0.000(4) C44 0.065(6) 0.030(5) 0.031(5) 0.000(4) -0.003(4) -0.011(4) C45 0.023(4) 0.018(4) 0.024(4) -0.001(3) 0.003(3) -0.002(3) C46 0.021(4) 0.021(4) 0.033(5) 0.006(4) -0.004(4) -0.003(3) C47 0.034(5) 0.016(4) 0.037(5) -0.008(4) -0.003(4) -0.001(3) C48 0.020(4) 0.042(5) 0.031(5) -0.013(4) 0.003(4) -0.011(4) C49 0.029(5) 0.033(5) 0.020(4) 0.003(4) 0.006(3) -0.011(4) C50 0.018(4) 0.021(4) 0.034(4) 0.002(4) 0.004(3) -0.008(3) N1 0.026(4) 0.018(3) 0.019(3) 0.005(3) 0.001(3) -0.003(3) N2 0.029(4) 0.015(3) 0.021(3) 0.000(3) -0.003(3) -0.003(3) O1 0.038(3) 0.015(3) 0.027(3) 0.007(2) -0.011(2) -0.007(2) O2 0.020(3) 0.016(3) 0.029(3) -0.002(2) -0.004(2) -0.004(2) O3 0.021(3) 0.019(3) 0.020(3) 0.006(2) 0.000(2) -0.008(2) O4 0.026(3) 0.015(3) 0.031(3) 0.005(2) 0.003(2) 0.001(2) O5 0.018(3) 0.021(3) 0.028(3) 0.001(2) -0.008(2) 0.001(2) O6 0.018(3) 0.021(3) 0.024(3) 0.000(2) 0.002(2) -0.001(2) _geom_special_details All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. 315
loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.281(8) . ? C1 O1 1.361(7) . ? C1 C4 1.535(9) . ? C2 O1 1.474(7) . ? C2 C14 1.523(9) . ? C2 C3 1.530(8) . ? C2 H2 1.0000 . ? C3 N1 1.476(8) . ? C3 C20 1.501(9) . ? C3 H3 1.0000 . ? C4 C9 1.519(8) . ? C4 C10 1.521(9) . ? C4 C5 1.570(9) . ? C5 C6 1.513(8) . ? C5 C11 1.544(8) . ? C5 H5 1.0000 . ? C6 O2 1.443(7) . ? C6 C7 1.514(8) . ? C6 H6 1.0000 . ? C7 O3 1.459(6) . ? C7 C8 1.488(9) . ? C7 H7 1.0000 . ? C8 C9 1.310(9) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.504(9) . ? C11 C12 1.546(8) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.373(9) . ? C14 C19 1.376(9) . ? C15 C16 1.407(10) . ? C15 H15 0.9500 . ? C16 C17 1.365(10) . ? C16 H16 0.9500 . ? C17 C18 1.372(10) . ? C17 H17 0.9500 . ? C18 C19 1.420(10) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.381(8) . ? C20 C21 1.402(9) . ? C21 C22 1.367(9) . ? C21 H21 0.9500 . ? C22 C23 1.388(9) . ? C22 H22 0.9500 . ? C23 C24 1.398(9) . ? C23 H23 0.9500 . ? C24 C25 1.393(9) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 N2 1.280(8) . ? C26 O4 1.353(8) . ? C26 C29 1.520(9) . ? C27 O4 1.477(7) . ? C27 C39 1.519(9) . ? C27 C28 1.529(9) . ? C27 H27 1.0000 . ? C28 N2 1.482(8) . ? C28 C45 1.504(9) . ? C28 H28 1.0000 . ? C29 C34 1.523(9) . ? 316
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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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Experimental for chapter 4.1 281 R
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Experimental for chapter 4.1 combin
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Experimental for chapter 4.1 3H, OB
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Page 263 and 264: Experimental for chapter 4.2 (1S*,2
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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 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: C4 0.025(4) 0.019(4) 0.018(4) 0.001
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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