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

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_atom_site_aniso_U_12 O1 0.0253(7) 0.0262(6) 0.0156(6) -0.0021(5) 0.0016(5) -0.0058(6) O2 0.0212(6) 0.0213(6) 0.0196(6) -0.0046(5) 0.0022(5) -0.0030(6) N1 0.0203(7) 0.0189(7) 0.0157(7) -0.0002(6) 0.0029(6) 0.0017(7) C1 0.0197(8) 0.0227(8) 0.0162(8) 0.0041(7) - 0.0015(7) 0.0051(8) C2 0.0173(8) 0.0212(9) 0.0146(8) 0.0015(7) - 0.0006(7) -0.0005(7) C3 0.0191(8) 0.0193(8) 0.0157(8) -0.0022(7) - 0.0003(7) -0.0009(7) C4 0.0193(9) 0.0195(8) 0.0160(8) 0.0003(7) 0.0005(7) 0.0017(7) C5 0.0174(8) 0.0161(8) 0.0163(8) 0.0009(7) 0.0019(7) -0.0016(7) C6 0.0199(9) 0.0145(7) 0.0181(8) 0.0000(7) 0.0000(7) 0.0013(7) C7 0.0233(9) 0.0205(9) 0.0145(8) -0.0018(7) 0.0027(7) 0.0023(8) C8 0.0179(8) 0.0214(8) 0.0231(9) -0.0013(7) 0.0040(7) 0.0008(7) C9 0.0158(8) 0.0226(9) 0.0233(9) -0.0037(7) - 0.0004(7) 0.0015(7) C10 0.0311(10) 0.0241(9) 0.0210(9) 0.0002(8) - 0.0004(8) 0.0069(9) C11 0.0179(8) 0.0196(8) 0.0172(8) -0.0039(7) 0.0018(7) 0.0023(7) C12 0.0241(9) 0.0190(8) 0.0192(8) -0.0001(7) 0.0001(8) 0.0011(8) C13 0.0197(10) 0.0258(10) 0.0345(10) - 0.0089(8) -0.0030(8) 0.0035(8) C14 0.0278(10) 0.0228(9) 0.0180(8) -0.0040(7) -0.0012(7) -0.0019(8) C15 0.0158(8) 0.0198(9) 0.0193(8) 0.0010(7) 0.0054(7) -0.0039(7) C16 0.0249(9) 0.0260(9) 0.0178(8) 0.0001(7) 0.0024(8) 0.0028(9) C17 0.0282(10) 0.0253(9) 0.0306(10) 0.0064(8) 0.0046(8) 0.0046(9) C18 0.0244(10) 0.0212(9) 0.0421(11) -0.0032(9) 0.0105(9) 0.0012(9) C19 0.0260(10) 0.0285(10) 0.0282(10) -0.0099(8) 0.0056(8) -0.0048(9) C20 0.0224(9) 0.0257(9) 0.0211(8) -0.0005(8) - 0.0001(8) -0.0026(8) C21 0.0189(8) 0.0179(8) 0.0171(8) 0.0008(7) - 0.0006(7) -0.0048(7) C22 0.0278(10) 0.0197(8) 0.0213(8) 0.0002(7) 0.0022(8) 0.0007(8) C23 0.0381(11) 0.0268(10) 0.0166(8) 0.0002(7) 0.0036(8) -0.0027(10) C24 0.0356(11) 0.0263(9) 0.0221(9) 0.0100(8) - 0.0019(8) -0.0037(9) C25 0.0279(10) 0.0216(9) 0.0326(10) 0.0045(8) 0.0012(8) 0.0021(9) C26 0.0246(10) 0.0225(9) 0.0217(9) -0.0013(7) 0.0046(8) 0.0000(8) _geom_special_details 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 O1 C1 1.365(2) . ? O1 C3 1.456(2) . ? O2 C6 1.366(2) . ? O2 C14 1.434(2) . ? N1 C1 1.269(2) . ? N1 C2 1.473(2) . ? C1 C4 1.514(2) . ? C2 C15 1.511(2) . ? C2 C3 1.564(2) . ? 301
C2 H2 1.0000 . ? C3 C21 1.506(2) . ? C3 H3 1.0000 . ? C4 C9 1.516(2) . ? C4 C10 1.550(3) . ? C4 C5 1.560(2) . ? C5 C6 1.520(2) . ? C5 C11 1.555(2) . ? C5 H5 1.0000 . ? C6 C7 1.336(3) . ? C7 C8 1.458(3) . ? C7 H7 0.9500 . ? C8 C9 1.330(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.524(2) . ? C11 C13 1.531(3) . ? 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 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.392(3) . ? C15 C20 1.394(2) . ? C16 C17 1.390(3) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.386(3) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.388(2) . ? C21 C26 1.393(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.388(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C3 106.24(13) . . ? C6 O2 C14 116.32(14) . . ? C1 N1 C2 107.28(14) . . ? N1 C1 O1 118.65(15) . . ? N1 C1 C4 126.28(16) . . ? O1 C1 C4 114.97(15) . . ? N1 C2 C15 113.53(13) . . ? N1 C2 C3 104.28(13) . . ? C15 C2 C3 113.13(14) . . ? N1 C2 H2 108.6 . . ? C15 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? O1 C3 C21 111.48(14) . . ? O1 C3 C2 103.38(13) . . ? C21 C3 C2 112.77(14) . . ? O1 C3 H3 109.7 . . ? 302
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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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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: H11 H 0.8924 0.9592 0.6829 0.022 Ui
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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