2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-tetrahydro-pyran-4-yl ester | 228873-39-0

• 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
• 英文名称: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxycarbonyloxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 228873-39-0
• 化学式: C₅₅H₇₄O₁₇
• 分子量: 1007.18
• InChiKey: FHQLXZJUNKFEMI-SVLPXNGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-tetrahydro-pyran-4-yl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6

文献信息

• An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate
  作者：Isao Azumaya、Toshihiro Niwa、Masaomi Kotani、Takamasa Iimori、Shiro Ikegami

  DOI：10.1016/s0040-4039(99)00843-6

  日期：1999.6

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.