methyl 2,6-di-O-pivaloyl-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-di-O-pivaloyl-α-D-mannopyranoside
• 英文别名: pivaloyl(-2)[pivaloyl(-6)]a-Man1Me；[(2R,3S,4S,5S,6S)-5-(2,2-dimethylpropanoyloxy)-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₁₇H₃₀O₈
• 分子量: 362.42
• InChiKey: ZEELWIKSMWAHQG-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,6-di-O-pivaloyl-α-D-mannopyranoside 在 native rabbit serum 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以33%的产率得到methyl 6-O-pivaloyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, intramolecular migrations and enzymic hydrolysis of partially pivaloylated methyl α-d-mannopyranosides

  摘要：

  A series of methyl O-pivaloyl-alpha-D-mannopyranosides was synthesized using pivaloyl chloride in pyridine. The 3,6-di-O-pivaloyl derivative 6 undergoes intramolecular transesterification in neutral conditions (buffer, pH 7.2) to give its 2,6-di-O-pivaloyl analogue 5. The course of this migration was followed using C-14-labelled 6. As opposed to 6 compound 5 was shown to be a good substrate for esterases present in rabbit serum. Thus, regioselective enzymic hydrolysis led to the preferential cleavage of the 2-OPiv group to yield a mixture of 2- and 6-O-monopivalates in a ratio of 1:2.6. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00501-3
• 作为产物：
  描述：

  三甲基乙酰氯 、 甲基-D-丙噻 以 吡啶 为溶剂， 反应 0.83h， 以49%的产率得到methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, intramolecular migrations and enzymic hydrolysis of partially pivaloylated methyl α-d-mannopyranosides

  摘要：

  A series of methyl O-pivaloyl-alpha-D-mannopyranosides was synthesized using pivaloyl chloride in pyridine. The 3,6-di-O-pivaloyl derivative 6 undergoes intramolecular transesterification in neutral conditions (buffer, pH 7.2) to give its 2,6-di-O-pivaloyl analogue 5. The course of this migration was followed using C-14-labelled 6. As opposed to 6 compound 5 was shown to be a good substrate for esterases present in rabbit serum. Thus, regioselective enzymic hydrolysis led to the preferential cleavage of the 2-OPiv group to yield a mixture of 2- and 6-O-monopivalates in a ratio of 1:2.6. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00501-3

文献信息

• Ljevakovic, Durdica; Parat, Dijana; Tomasic, Jelka, Croatica Chemica Acta, 1995, vol. 68, # 3, p. 477 - 484
  作者：Ljevakovic, Durdica、Parat, Dijana、Tomasic, Jelka、Tomic, Srdanka

  DOI：——

  日期：——
• Synthesis, intramolecular migrations and enzymic hydrolysis of partially pivaloylated methyl α-d-mannopyranosides
  作者：Srđanka Tomić、Vesna Petrović、Maja Matanović

  DOI：10.1016/s0008-6215(02)00501-3

  日期：2003.3

  A series of methyl O-pivaloyl-alpha-D-mannopyranosides was synthesized using pivaloyl chloride in pyridine. The 3,6-di-O-pivaloyl derivative 6 undergoes intramolecular transesterification in neutral conditions (buffer, pH 7.2) to give its 2,6-di-O-pivaloyl analogue 5. The course of this migration was followed using C-14-labelled 6. As opposed to 6 compound 5 was shown to be a good substrate for esterases present in rabbit serum. Thus, regioselective enzymic hydrolysis led to the preferential cleavage of the 2-OPiv group to yield a mixture of 2- and 6-O-monopivalates in a ratio of 1:2.6. (C) 2003 Elsevier Science Ltd. All rights reserved.