(3S,4S)-3,4-二羟基-L-脯氨酸 | 23161-63-9

• 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
• 中文名称: (3S,4S)-3,4-二羟基-L-脯氨酸
• 英文名称: 2,3-cis-3,4-trans-3,4-dihydroxy-L-proline
• 英文别名: 2,3-cis-3,4-trans-Dihydroxy-L-prolin；L-2,3-cis-3,4-trans-dihydroxyproline；(2S,3S,4S)-3,4-dihydroxyproline；2,3-cis-3,4-trans-3,4-Dihydroxy-L-prolinq；(2S,3S,4S)-3,4-dihydroxypyrrolidine-2-carboxylic acid
• CAS: 23161-63-9
• 化学式: C₅H₉NO₄
• 分子量: 147.131
• InChiKey: HWNGLKPRXKKTPK-YVZJFKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-阿拉伯糖 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium hypochlorite 、 sodium chlorite 、 sodium dihydrogenphosphate 、 锂硼氢 、 甲酸 、 Tesser's base 、 氢溴酸 、 氢气 、 溴 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 168.0h， 生成 (3S,4S)-3,4-二羟基-L-脯氨酸
  参考文献：
  名称：

  The conversion of pentoses to 3,4-dihydroxyprolines

  摘要：

  The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproli ne was synthesized from L-arabinose in 10 steps and 31 % overall yield. The same series of reactions was employed to convert L-xylose to L-2,3trans-3,4-trans-3,4-dihydroxyproline. Orthogonally protected versions of these amino acids were produced on gram scale, en route to the free amino acids, and these will serve as versatile intermediates in peptide synthesis. This synthetic strategy involved N alpha-Fmoc protection and protection of the C3 and C4 secondary alcohols as methoxyethoxymethyl (MEM) ethers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.072

文献信息

• Stereoselective Synthesis of 3,4-Dihydroxylated Prolines and Prolinols Starting from<scp>L</scp>-Tartaric Acid
  作者：M. Oba、S. Koguchi、K. Nishiyama

  DOI：10.1002/jhet.1634

  日期：2014.1

  A straightforward and stereoselective synthesis of 3,4‐dihydroxyprolines and 3,4‐dihydroxyprolinols is described. The key reaction in this synthesis is a protective group‐controlled diastereoselective cyanation of a chiral acyliminium intermediate derived from l‐tartaric acid. Methanolysis of the obtained cyanolactam gave methyl 3,4‐dihydroxypyroglutamate that was converted to 3,4‐dihydroxyproline

  描述了3,4-二羟基脯氨酸和3,4-二羟基脯氨酸的直接和立体选择性合成。该合成中的关键反应是衍生自l酒石酸的手性酰基中间体的保护基控制的非对映选择性氰化。所获得的氰基内酰胺的甲醇解产生3,4-二羟基焦谷氨酸甲酯，通过逐步还原内酰胺羰基和酯基，可将其转化为3,4-二羟基脯氨酸和3,4-二羟基脯氨酸。
• Synthesis of (3S,4S)-3,4-Dihydroxyprolines from L-Tartaric Acid.
  作者：Yasushi ARAKAWA、Shigeyuki YOSHIFUJI

  DOI：10.1248/cpb.39.2219

  日期：——

  Natural (2S, 3S, 4S)-3, 4-dihydroxyproline (1) and the new (2R, 3S, 4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.

  通过环状席夫碱的氰基甲硅烷基化，由 L-酒石酸合成了天然 (2S, 3S, 4S)-3, 4-二羟基脯氨酸 (1) 和新的 (2R, 3S, 4S)-异构体 (7)。
• Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars
  作者：Carol M. Taylor、William D. Barker、Claudette A. Weir、Jae H. Park

  DOI：10.1021/jo025538x

  日期：2002.6.1

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.
• Kahl, Jens-Uwe; Wieland, Theodor, Liebigs Annalen der Chemie, 1981, # 8, p. 1445 - 1450
  作者：Kahl, Jens-Uwe、Wieland, Theodor

  DOI：——

  日期：——
• Efficient syntheses of naturally occurring 3,4-dihydroxyprolines: Electrophile-mediated lactonization of 2-amino-3-hydroxy-4-pentenoic acid derivatives
  作者：Yasufumi Ohfune、Natsuko Kurokawa

  DOI：10.1016/s0040-4039(00)95023-8

  日期：——