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

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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 C7 1.423(5) . ? O1 H1 0.8400 . ? O2 C3 1.441(5) . ? O2 H2 0.8400 . ? O3 C4 1.434(5) . ? O3 H3 0.8400 . ? O4 C5 1.435(5) . ? O4 H4 0.8400 . ? O5 C6 1.443(6) . ? O5 H5 0.8400 . ? C1 C8 1.541(6) . ? C1 C6 1.547(6) . ? C1 C7 1.551(7) . ? C1 C2 1.564(6) . ? C2 C3 1.540(6) . ? C2 C9 1.562(6) . ? C2 H2A 1.0000 . ? C3 C4 1.505(6) . ? C3 H3A 1.0000 . ? C4 C5 1.503(6) . ? C4 H4A 1.0000 . ? C5 C6 1.520(6) . ? C5 H5A 1.0000 . ? C6 H6 1.0000 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.524(6) . ? C9 C10 1.547(7) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O6 C18 1.423(5) . ? O6 H6A 0.8400 . ? O7 C14 1.427(6) . ? O7 H7 0.8400 . ? O8 C15 1.443(5) . ? O8 H8 0.8400 . ? O9 C16 1.420(5) . ? O9 H9A 0.8400 . ? O10 C17 1.446(5) . ? O10 H10 0.8400 . ? C12 C19 1.536(6) . ? C12 C18 1.539(6) . ? C12 C17 1.544(6) . ? C12 C13 1.575(7) . ? C13 C14 1.549(6) . ? C13 C20 1.569(6) . ? C13 H13 1.0000 . ? C14 C15 1.520(6) . ? C14 H14 1.0000 . ? C15 C16 1.502(6) . ? C15 H15 1.0000 . ? C16 C17 1.535(6) . ? C16 H16 1.0000 . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.533(7) . ? C20 C22 1.534(7) . ? C20 H20 1.0000 . ? 331
C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O1S H1S 0.78(6) . ? O1S H2S 0.91(5) . ? O2S H3S 0.93(6) . ? O2S H4S 0.93(7) . ? 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 C7 O1 H1 109.5 . . ? C3 O2 H2 109.5 . . ? C4 O3 H3 109.5 . . ? C5 O4 H4 109.5 . . ? C6 O5 H5 109.5 . . ? C8 C1 C6 107.7(4) . . ? C8 C1 C7 109.0(4) . . ? C6 C1 C7 108.4(4) . . ? C8 C1 C2 110.7(4) . . ? C6 C1 C2 111.3(4) . . ? C7 C1 C2 109.8(4) . . ? C3 C2 C9 114.0(4) . . ? C3 C2 C1 112.9(4) . . ? C9 C2 C1 113.6(4) . . ? C3 C2 H2A 105.1 . . ? C9 C2 H2A 105.1 . . ? C1 C2 H2A 105.1 . . ? O2 C3 C4 108.6(4) . . ? O2 C3 C2 109.0(3) . . ? C4 C3 C2 111.8(4) . . ? O2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? O3 C4 C5 108.7(4) . . ? O3 C4 C3 110.3(4) . . ? C5 C4 C3 112.8(4) . . ? O3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? O4 C5 C4 112.0(4) . . ? O4 C5 C6 106.4(4) . . ? C4 C5 C6 111.3(4) . . ? O4 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? O5 C6 C5 108.8(4) . . ? O5 C6 C1 108.1(4) . . ? C5 C6 C1 112.8(4) . . ? O5 C6 H6 109.0 . . ? C5 C6 H6 109.0 . . ? C1 C6 H6 109.0 . . ? O1 C7 C1 112.6(4) . . ? O1 C7 H7A 109.1 . . ? C1 C7 H7A 109.1 . . ? O1 C7 H7B 109.1 . . ? C1 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 109.6(4) . . ? C11 C9 C2 111.9(4) . . ? C10 C9 C2 114.1(4) . . ? C11 C9 H9 106.9 . . ? C10 C9 H9 106.9 . . ? 332
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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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Experimental for chapter 4.2 (1S*,2
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Experimental for chapter 4.2 10.0,
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Experimental for chapter 4.2 cm 3 )
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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 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: C3 0.015(3) 0.016(3) 0.021(3) -0.00
Page 333 and 334: H21A C21 H21C 109.5 . . ? H21B C21
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