(E)-Ethyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-6-O-methanesulfonyl-D-manno-oct-2-enoate | 130947-76-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-Ethyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-6-O-methanesulfonyl-D-manno-oct-2-enoate
• 英文别名: ethyl (E)-3-[(4R,5R)-5-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-methylsulfonyloxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 130947-76-1
• 化学式: C₁₇H₂₈O₉S
• 分子量: 408.47
• InChiKey: BJODXMSBPLJLQH-WQINFNIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-Ethyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-6-O-methanesulfonyl-D-manno-oct-2-enoate 在 lithium aluminium tetrahydride 、 氨 作用下， 以 乙醇 为溶剂， 反应 336.17h， 生成 2,3,6-Trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octitol
  参考文献：
  名称：

  Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

  摘要：

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.

  DOI：

  10.1016/s0040-4020(01)90234-0
• 作为产物：
  描述：

  甲基磺酰氯 、 (Z)-3-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester 在 吡啶 作用下， 生成 (E)-Ethyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-6-O-methanesulfonyl-D-manno-oct-2-enoate
  参考文献：
  名称：

  Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

  摘要：

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.

  DOI：

  10.1016/s0040-4020(01)90234-0

文献信息

• Robina, Inmaculada; Gearing, Patrick R.; Buchanan, J. Grant, Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2622 - 2624
  作者：Robina, Inmaculada、Gearing, Patrick R.、Buchanan, J. Grant、Wightman, Richard H.

  DOI：——

  日期：——
• ROBINA, INMACULADA;GEARING, R. PATRICK;BUCHANAN, J. GRANT;WIGHTMAN, RICHA+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2622-2624
  作者：ROBINA, INMACULADA、GEARING, R. PATRICK、BUCHANAN, J. GRANT、WIGHTMAN, RICHA+

  DOI：——

  日期：——
• Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems
  作者：Deryk K. Thompson、Christine N. Hubert、Richard H. Wightman

  DOI：10.1016/s0040-4020(01)90234-0

  日期：1993.4

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.