Acetic acid (2S,4S,6R)-6-acetoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester | 183952-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Acetic acid (2S,4S,6R)-6-acetoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 183952-43-4
• 化学式: C₁₇H₃₂O₆Si
• 分子量: 360.523
• InChiKey: JNGUMVFGCRRPFW-PHZGNYQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,4S,6R)-6-acetoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester 在 Candida antarctica lipase 、 phosphate buffer pH = 7.0 、 Triton X-100 作用下， 以 水 为溶剂， 反应 6.0h， 以70%的产率得到[(2S,4R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans

  摘要：

  The stereoselective acylation of meso-tetrahydropyrans 6 and 7 by enol eaters (vinyl acetate or isopropenyl acetate) in the presence of Candida antarctica lipase in organic media gave the corresponding (2R,4S,6S)monoesters 10 and 11 in high enantiomeric purity. The hydrolysis of the corresponding diacetate derivatives 8 and 9 in the presence of the same enzyme provided the opposite enantiomers, (2S,4R,6R)-monoesters 10 and 11. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00460-1
• 作为产物：
  描述：

  (2S*,6R*)-cis-2,6-bis(ethoxycarbonyl)-γ-tetrahydropyranol 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 Acetic acid (2S,4S,6R)-6-acetoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans

  摘要：

  The stereoselective acylation of meso-tetrahydropyrans 6 and 7 by enol eaters (vinyl acetate or isopropenyl acetate) in the presence of Candida antarctica lipase in organic media gave the corresponding (2R,4S,6S)monoesters 10 and 11 in high enantiomeric purity. The hydrolysis of the corresponding diacetate derivatives 8 and 9 in the presence of the same enzyme provided the opposite enantiomers, (2S,4R,6R)-monoesters 10 and 11. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00460-1

文献信息

• Lipase mediated desymmetrization of meso-2,6-di(acetoxymethyl)-tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides
  作者：Thomas F.J. Lampe、H.M.R. Hoffmann、Uwe T. Bornscheuer

  DOI：10.1016/0957-4166(96)00380-1

  日期：1996.10

  The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction. Copyright (C) 1996 Elsevier Science Ltd