methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside | 86651-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside
• 英文别名: Methyl-3,6-di-O-pivaloyl-α-D-mannopyranosid；Methyl 3,6-di-o-pivaloyl-alpha-d-mannopyranoside；[(2R,3R,4S,5S,6S)-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxy-6-methoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 86651-41-4
• 化学式: C₁₇H₃₀O₈
• 分子量: 362.42
• InChiKey: MSLAYKHBJRUPHD-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 3,6-di-O-pivaloyl-α-D-mannopyranoside 在 甲醇 、 硼氘化钠 、 4 A molecular sieve 、 sodium acetate 、 sodium 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 84.75h， 生成 Methyl-α-D-<2-D₁>-glucopyranosid
  参考文献：
  名称：

  Klausener, Alexander; Runsink, Jan; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1984, # 4, p. 783 - 790

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基乙酰氯 、 甲基-D-丙噻 以 吡啶 、 二氯甲烷 为溶剂， 以81.5%的产率得到methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside
  参考文献：
  名称：

  A simple preparation of methyl 2,6-dideoxy- and methyl 3,6-dideoxy-α-d-arabino-hexopyranoside by photochemical deoxygenation

  摘要：

  DOI：

  10.1016/0008-6215(83)88119-1

文献信息

• Synthesis of peptidomimetics based on iminosugar and β-d-glucopyranoside scaffolds and inhibiton of HIV-protease
  作者：Florence Chery、Linda Cronin、Julie L O'Brien、Paul V Murphy

  DOI：10.1016/j.tet.2004.05.080

  日期：2004.7

  Synthetic routes to peptidomimetic compounds derived from saccharide scaffolds are described. The regioselective introduction of pivaloyl groups was achieved from N-benzyloxycarbonyl protected 1-deoxymannojirimycin or via D-fructopyranosides. The results from biological evaluation of the saccharide derivatives as HIV-protease inhibitors are included. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of an iminosugar based peptidomimetic analogue
  作者：Florence Chery、Paul V. Murphy

  DOI：10.1016/j.tetlet.2004.01.064

  日期：2004.3

  The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
• Regioselective Acylation of Hexopyranosides with Pivaloyl Chloride
  作者：Lu Jiang、Tak-Hang Chan

  DOI：10.1021/jo980294v

  日期：1998.8.1
• 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.