(4S,5R)-3-N-tert-butyloxycarbonyl-4-methoxycarbonyl-5-((1"R,3"Z)-1"-methylpent-3"-enyl)-2,2-dimethyl-1,3-oxazolidine | 192129-63-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-3-N-tert-butyloxycarbonyl-4-methoxycarbonyl-5-((1"R,3"Z)-1"-methylpent-3"-enyl)-2,2-dimethyl-1,3-oxazolidine
• 英文别名: 3-O-tert-butyl 4-O-methyl (4S,5R)-5-[(Z,2R)-hex-4-en-2-yl]-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate
• CAS: 192129-63-8
• 化学式: C₁₈H₃₁NO₅
• 分子量: 341.448
• InChiKey: XGYXRVHWUMUJRC-GQODHHKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-N-tert-butyloxycarbonyl-4-methoxycarbonyl-5-((1"R,3"Z)-1"-methylpent-3"-enyl)-2,2-dimethyl-1,3-oxazolidine 在 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (4S,5R)-5-((Z)-(R)-1-Methyl-pent-3-enyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

  摘要：

  A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral alpha,beta-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00164-x
• 作为产物：
  描述：

  3-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-N,2-O-isopropylidene-D-threose 在 sodium chlorite 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 氨基磺酸 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 69.75h， 生成 (4S,5R)-3-N-tert-butyloxycarbonyl-4-methoxycarbonyl-5-((1"R,3"Z)-1"-methylpent-3"-enyl)-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

  摘要：

  A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral alpha,beta-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00164-x

文献信息

• Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition
  作者：Arounarith Tuch、Michèle Saniìere、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/s0957-4166(97)00164-x

  日期：1997.5

  A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral alpha,beta-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (C) 1997 Elsevier Science Ltd.