(2,2,4-trimethyl-1,3-dioxolane-4-yl)methyl methanesulfonate | 365513-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,2,4-trimethyl-1,3-dioxolane-4-yl)methyl methanesulfonate
• 英文别名: [(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate
• CAS: 365513-14-0
• 化学式: C₈H₁₆O₅S
• 分子量: 224.278
• InChiKey: XSJHLFITRCFYLP-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,2,4-trimethyl-1,3-dioxolane-4-yl)methyl methanesulfonate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-(2,3-dihydroxy-2-methyl)propyl methanesulfonate
  参考文献：
  名称：

  An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  摘要：

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00230-0
• 作为产物：
  描述：

  methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2,2,4-trimethyl-1,3-dioxolane-4-yl)methyl methanesulfonate
  参考文献：
  名称：

  An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  摘要：

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00230-0

文献信息

• An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives
  作者：Alberto Avenoza、Carlos Cativiela、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(01)00230-0

  日期：2001.6

  This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (X)-2-methylglycidol. (C) 2001 Elsevier Science Ltd. All rights reserved.