2-((2R,3R,4R,5R)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-ethanol | 595559-92-5

• 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: 2-((2R,3R,4R,5R)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-ethanol
• 英文别名: 2-[(2R,3R,4R,5R)-1-benzyl-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-yl]ethanol
• CAS: 595559-92-5
• 化学式: C₃₅H₃₉NO₄
• 分子量: 537.699
• InChiKey: YDBYISLGJSBYRH-BAQBVXSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((2R,3R,4R,5R)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-ethanol 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 以40%的产率得到2,5-imino-2,5,6-trideoxy-D-manno-heptitol
  参考文献：
  名称：

  Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer: absolute stereochemistry of natural products from Hyacinthus orientalis

  摘要：

  A concise enantioselective synthesis of 2,5-imino-2,5,6-trideoxy-D-manno-heptitol (6-deoxy-homoDMDP) and 2,5-imino-2,5,6-trideoxy-L-gulo-heptitol has been achieved. These compounds were used as stereochemical references to establish the absolute configuration of the corresponding naturally occurring stereoisomers, recently isolated from Hyacinthus orientalis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00081-2
• 作为产物：
  描述：

  (2S,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-methoxyoxolane 在 吡啶 、 盐酸 、 4 A molecular sieve 、 硫酸 、 臭氧 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 2-((2R,3R,4R,5R)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-ethanol
  参考文献：
  名称：

  Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer: absolute stereochemistry of natural products from Hyacinthus orientalis

  摘要：

  A concise enantioselective synthesis of 2,5-imino-2,5,6-trideoxy-D-manno-heptitol (6-deoxy-homoDMDP) and 2,5-imino-2,5,6-trideoxy-L-gulo-heptitol has been achieved. These compounds were used as stereochemical references to establish the absolute configuration of the corresponding naturally occurring stereoisomers, recently isolated from Hyacinthus orientalis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00081-2