(2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone | 292177-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone
• 英文别名: (+)-(3S,4S)-3,4-dihydroxy-3-methyldihydrofuran-2-one；(3S,4S)-3,4-dihydroxy-3-methyldihydrofuran-2-one；2-C-methyl-L-erythrono-1,4-lactone；(+)-(2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone；(3S,4S)-3,4-dihydroxy-3-methyloxolan-2-one
• CAS: 292177-96-9
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: OHTGZAWPVDWARE-UCORVYFPSA-N

物化性质

• 沸点：
  254.0±7.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone 在 氢氧化钾 、 水 作用下， 反应 0.33h， 以100%的产率得到potassium (2RS,3RS)-2,3,4-trihydroxy-2-methylbutanoate
  参考文献：
  名称：

  A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate

  摘要：

  A series of 1,2-dioxanes 3 were ring-opened with Co-(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2C-D-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.

  DOI：

  10.1021/jo900392y
• 作为产物：
  描述：

  2-methyl-2,3,4-trihydroxy-butanoic acid-1,4-lactone 在 吡啶 、 4-二甲氨基吡啶 、 Amano PS-1400 lipase 、 potassium carbonate 、 sodium phosphate 作用下， 以 甲醇 、 水 、 Petroleum ether 、 苯 为溶剂， 反应 41.0h， 生成 (2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025

文献信息

• Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide
  作者：David J. Hotchkiss、Raquel Soengas、Kathrine V. Booth、Alexander C. Weymouth-Wilson、Vanessa Eastwick-Field、George W.J. Fleet

  DOI：10.1016/j.tetlet.2006.11.137

  日期：2007.1

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.
• WO2007/25304
  申请人：——

  公开号：——

  公开（公告）日：——
• An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate
  作者：Sanjib Gogoi、Narshinha P. Argade

  DOI：10.1016/j.tetasy.2006.02.025

  日期：2006.3

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.
• A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the Leaf-Closing Substance Potassium (±)-(2<i>R</i>,3<i>R</i>)-2,3,4-Trihydroxy-2-methylbutanoate
  作者：Daniel Sejer Pedersen、Tony V. Robinson、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo900392y

  日期：2009.6.5

  A series of 1,2-dioxanes 3 were ring-opened with Co-(SALEN)(2) to furnish lactol regioisomers 4 and 5 (86-99% yield). The lactols were oxidized to gamma-lactones 8 and 9 (72-96% yield) and deprotected to afford the 2-C- and 3-C-alkyl and aryl branched erythrono-gamma-lactones 1, 6, and 7 (65-94% yield), including the natural plant lactone (+/-)-2C-D-methylerythrono-1,4-lactone 1. The latter compound was treated with aqueous potassium hydroxide to afford potassium (+/-)-(2R,3R)-2,3,4-trihydroxy-2-methylbutanoate 2, which is a leaf-closing substance of Leucaena leucocephalam.