methyl (4R)-4-methyl-2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylate | 356048-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: methyl (4R)-4-methyl-2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylate
• 英文别名: methyl (4R)-4-methyl-2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylate
• CAS: 356048-06-1
• 化学式: C₅H₈O₆S
• 分子量: 196.181
• InChiKey: LIAOXSZDFVJVFM-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-methyl-2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylate 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 120.0h， 生成 (2S)-2-氨基-3-羟基-2-甲基丙酸甲酯
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

  摘要：

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha -methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary alpha -amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-alpha -methylserinal building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00159-8
• 作为产物：
  描述：

  methyl (R)-2,3-dihydroxy-2-methylpropanoate 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 methyl (4R)-4-methyl-2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

  摘要：

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha -methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary alpha -amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-alpha -methylserinal building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00159-8