(Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose | 294172-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose
• 英文别名: tert-butyl (3aR,4S,6aS)-4-[(2Z)-2-[(1R,2R,4R,5R)-2-hydroxy-4-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-3-ylidene]ethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 294172-63-7
• 化学式: C₂₇H₃₇NO₈
• 分子量: 503.593
• InChiKey: YHMFUNZDVPSGMF-SRNOFYRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到(Z)-1,6-anhydro-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099
• 作为产物：
  描述：

  3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose 在 lithium aluminium tetrahydride 、 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.75h， 生成 (Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099

文献信息

• Marquis, Christian; Cardona, Francesca; Robina, Inmaculada, Heterocycles, 2002, vol. 56, # 1-2, p. 181 - 208
  作者：Marquis, Christian、Cardona, Francesca、Robina, Inmaculada、Wurth, Gaby、Vogel, Pierre

  DOI：——

  日期：——