(-)-5-C-(Benzyloxycarbonyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranose | 144367-17-9

• 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: (-)-5-C-(Benzyloxycarbonyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranose
• 英文别名: benzyl (2S,3S)-2-[(3aS,4S,6S,6aS)-4-hydroxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoate
• CAS: 144367-17-9；144408-63-9
• 化学式: C₂₂H₃₀O₉
• 分子量: 438.475
• InChiKey: MTRPMHHUTJPOLL-RRORWFOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-5-C-(Benzyloxycarbonyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranose 在 palladium on activated charcoal 2,6-二甲基吡啶 、 叠氮磷酸二苯酯 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 (+)-tert-Butyldimethylsilyl 5--6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranoside
  参考文献：
  名称：

  Total syntheses of 1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol and (1S,2R,6R,7R,8S,8aS)-pentahydroxyindolizidine

  摘要：

  DOI：

  10.1016/s0040-4039(00)61233-9
• 作为产物：
  描述：

  (1R,4R,5S,6S,7S)-4-exo-<(1'S,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl>-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo<3.2.1>octan-3-one 、 苯甲醇 在 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 以76%的产率得到(-)-5-C-(Benzyloxycarbonyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranose
  参考文献：
  名称：

  Total syntheses of 1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol and (1S,2R,6R,7R,8S,8aS)-pentahydroxyindolizidine

  摘要：

  DOI：

  10.1016/s0040-4039(00)61233-9

文献信息

• Total Asymmetric Syntheses of 1,5-Dideoxy-1,5-iminooctitols and 1,2,6,7,8-Pentahydroxyindolizidines
  作者：Yuanwei Chen、Pierre Vogel

  DOI：10.1021/jo00088a033

  日期：1994.5

  (1R,4R,5S,6S,7S)-4-exo-[(1'S,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl]-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo[3.2.1]octan-3-one ((+)-5) and its diastereomer (1S,4S,5R,6R,7R)-(1'R,2'R)-(-)-30 derived from (R)-2,3-O-isopropylideneglyceraldehyde and (+/-)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo[2.2.1]hept-2-one were alcoholyzed with benzyl alcohol in CCl4 (CsF as base) into the corresponding 5-C-(benzyloxycarbonly)-5-deoxyoctofuranoses (+)-9 and (-)-31 which were converted via Curtius rearrangements into (-)-1,5-dideoxy-1,5-imino-D-erythro-D-talo-octitol ((-)-20) and its D-threo-L-talo isomer (+)-36, respectively, Alcoholyses of (+)-5 and (-)-30 with benzyl alcohol in DMSO in the presence of CsF or K2CO3 led to the epimerized benzyl esters (-)-10 and (-)-38, respectively, which were converted into (-)-1,5-didoexy-1,5-imino-D-erythro-6-allo-octitol ((-)-27) and its D-threo-D-allo isomer (+)-42. The 1,5-dideoxy-1,5-iminooctitols were converted into the corresponding 1,2,6,7,8-pentahydroxyindolizidines in a single step.

  (1R,4R,5S,6S,7S)-4-exo-[(1'S,2'R)-1'-羟基-2',3'-(异丙叉二氧基)丙基]-6-exo,7-exo-(异丙叉二氧基)-2,8-二氧杂双环[3.2.1]辛烷-3-酮 ((+)-5) 及其对映体 (1S,4S,5R,6R,7R)-(1'R,2'R)-(-)-30，源自 (R)-2,3-O-异丙叉甘油醛和 (+/-)-5-exo,6-exo-(异丙叉二氧基)-7-氧杂双环[2.2.1]庚-2-酮，经在四氯化碳（铯氟化物作为碱）中与苯甲醇进行醇解，生成相应的 5-C-(苯甲氧基羰基)-5-去氧代八糖呋喃糖苷 (+)-9 和 (-)-31。后者经卡特里乌斯重排转化为 (-)-1,5-二去氧-1,5-亚胺-D-赤-L-塔罗八糖醇 ((-)-20) 和其 D-赤-L-塔罗异构体 (+)-36。此外，(+)-5 和 (-)-30 在二甲基亚砜中、在铯氟化物或碳酸钾存在下与苯甲醇醇解，生成构型互变的苯甲酸酯 (-)-10 和 (-)-38，进而转化为 (-)-1,5-二去氧-1,5-亚胺-D-赤-6-阿洛八糖醇 ((-)-27) 和其 D-赤-D-阿洛异构体 (+)-42。1,5-二去氧-1,5-亚胺八糖醇随后单步转化为相应的 1,2,6,7,8-五羟基吲哚嗪。
• Total syntheses of 1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol and (1S,2R,6R,7R,8S,8aS)-pentahydroxyindolizidine
  作者：Chen Yuanwei、Pierre Vogel

  DOI：10.1016/s0040-4039(00)61233-9

  日期：1992.8