meso-(2S,3S,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride | 143300-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: meso-(2S,3S,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride
• 英文别名: (2R,3R,4S,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine hydrochloride；meso-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride；2,5-dideoxy-2,5-imino-D-allitol
• CAS: 143300-65-6；872345-53-4
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: ASOISZHLRDHELT-ZSAATHKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.95
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-vinylpyrrolidine 在 盐酸 、 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 为溶剂， 生成 meso-(2S,3S,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride
  参考文献：
  名称：

  Stereocontrolled synthesis of 1,7a-diepialexine

  摘要：

  (S)-吡咯谷氨酸衍生物4已被用于合成(2R,5R)-二羟甲基-(3R,4S)-二羟基吡咯啶衍生物15、1,7a-二环乙基嘌呤1和1,7,7a-三环乙基嘌呤2。

  DOI：

  10.1016/s0040-4039(00)92240-8

文献信息

• Synthesis of <scp>d</scp>- and <scp>l</scp>-2,3-<i>trans</i>-3,4-<i>cis</i>-4,5-<i>trans</i>-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them
  作者：Antonio J. Moreno-Vargas、Inmaculada Robina、Elena Petricci、Pierre Vogel

  DOI：10.1021/jo049637h

  日期：2004.6.1

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.
• Polyhydroxylated pyrrolidines, III. Synthesis of new protected 2,5-dideoxy-2,5-iminohexitols from d-fructose
  作者：Isidoro Izquierdo、María T. Plaza、Miguel Rodríguez、Francisco Franco、Alicia Martos

  DOI：10.1016/j.tet.2005.09.043

  日期：2005.12

  The readily available 3-O-benzoyl-4-O-benzyl-1,2-Oisopi-opylidene-beta-D-fructopyranose (6) was straightforwardly transformed into 5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-beta-D-fructopyranose (8), after treatment under modified Garegg's conditions followed by reaction of the resulting 3-O-benzoyl-4-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-L-sorbopyranose (7) with lithium azide in DMF O-debenzoylation at C(3) in 8, followed by oxidation and reduction caused the inversion of the configuration to afford the corresponding beta-D-psicopyranose derivative 11 that was transformed into the related 3,4-di-O-benzyl derivative 12. Cleavage of the acetonide of 12 to give 13 followed by O-tert-butyldiphenylsilylation afforded a resolvable mixture of 14 and 15. Compound 14 was transformed into (2R,3R,4S,5R)- (17) and (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (18) either by a tandem Staudinger/intramolecular aza-Wittig process and reduction of the resulting intermediate 2 only into 18 by a high stereoselective catalytic hydrogenation. When 15 was subjected to the same protocol, (2S,3S,4R,5R)- (21) and (2R,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (22) were obtained, respectively. (c) 2005 Elsevier Ltd. All rights reserved.