(2R,2'R,3'S,4'R)-2-hydroxy-2-(3',4'-dihydroxypyrrolidin-2'-yl)ethanoic acid | 766481-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,2'R,3'S,4'R)-2-hydroxy-2-(3',4'-dihydroxypyrrolidin-2'-yl)ethanoic acid
• 英文别名: 3,6-dideoxy-3,6-imino-D-allonic acid；(2R)-2-[(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-hydroxyacetic acid
• CAS: 766481-26-9
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: CMDOGOPKNMVQTC-TXICZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,2'R,3'S,4'R)-2-hydroxy-2-(3',4'-dihydroxypyrrolidin-2'-yl)ethanoic acid 在 sodium tetrahydroborate 、 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1,4-Dideoxy-1,4-imino-L-allitol Hydrochloride
  参考文献：
  名称：

  Lundt; Madsen, Synthesis, 1993, # 7, p. 714 - 720

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-dideoxy-3,6-imino-D-allonamide hydrobromide 在 氢溴酸 作用下， 以 水 为溶剂， 以79%的产率得到(2R,2'R,3'S,4'R)-2-hydroxy-2-(3',4'-dihydroxypyrrolidin-2'-yl)ethanoic acid
  参考文献：
  名称：

  Lundt; Madsen, Synthesis, 1993, # 7, p. 714 - 720

  摘要：

  DOI：

文献信息

• Asymmetric syntheses of polysubstituted homoprolines and homoprolinols
  作者：Kristína Csatayová、Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、J. Gair Ford、James A. Lee、Paul M. Roberts、Benjamin G. Saward、Haewon Song、James E. Thomson

  DOI：10.1016/j.tet.2015.10.005

  日期：2015.12

  Complementary protocols for the diastereoselective syn- and anti-dihydroxylations of enantiopure dihydropyrrole scaffolds were used as the key steps in the asymmetric syntheses of several polysubstituted homoprolines and homoprolinols. The requisite dihydropyrroles were prepared in three steps from commercially available sorbic acid via either hydroamination or aminohydroxylation of the corresponding tert-butyl ester, followed by ring-closing metathesis. Subsequent olefinic oxidation and deprotection gave access to the corresponding enantiopure homoprolines [(2S,3S,4R)-dihydroxyhomoproline, (2S,3R,4R)-dihydroxyhomoproline and (S,S,S)-3-amino-4-hydroxy-homoproline], enantiopure alpha-hydroxy-homoprolines [3,6-dideoxy-3,6-imino-D-allonic acid and 3,6-dideoxy-3,6-imino-D-gulonic acid] and enantiopure homoprolinols [1,4-dideoxy-1,4-imino-L-allitol and (S,S,S)-3-amino-4-hydroxyhomoprolinol] as single diastereoisomers in good overall yields. (C) 2015 Elsevier Ltd. All rights reserved.