1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose | 108257-55-2

• 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: 1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose
• 英文别名: (2S,3R,4S,5R,6R)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetra-acetate；[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 108257-55-2
• 化学式: C₂₁H₂₆O₁₀
• 分子量: 438.431
• InChiKey: AQOFYCKDAMGIKL-YMQHIKHWSA-N

物化性质

• 沸点：
  499.4±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose 、 sodium methylate 、 以 甲醇 为溶剂， 反应 16.0h， 以Concentration of the resulting solution gave (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (2.17 g)的产率得到苄基 alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Amphetamine Prodrugs

  摘要：

  本发明涉及一种安非他命前药，其提供安非他命的结肠释放。

  公开号：

  US20140073589A1
• 作为产物：
  描述：

  D-葡萄糖 在 吡啶 、 三氟乙酸 、 silver(l) oxide 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 3.49h， 生成 1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  Utamura, Toshiko; Kuromatsu, Keiko; Suwa, Kiyoko, Chemical and pharmaceutical bulletin, 1986, vol. 34, p. 2341 - 2353

  摘要：

  DOI：

文献信息

• A practical approach to regioselective O-benzylation of primary positions of polyols
  作者：Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1016/j.tetlet.2013.01.023

  日期：2013.3

  Exposure of saccharide polyols to a moderate excess of benzyl bromide and DIPEA at 90 degrees C results in the regioselective O-benzylation of primary positions in moderate to good yields. The reactions can be performed without inert atmosphere and provide synthetically useful yields within a few hours. (c) 2013 Elsevier Ltd. All rights reserved.
• Rapid Preparation of Variously Protected Glycals Using Titanium(III)
  作者：Roxanne P. Spencer、Cullen L. Cavallaro、Jeffrey Schwartz

  DOI：10.1021/jo982447k

  日期：1999.5.1

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.
• The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents
  作者：Sinele B. Tsabedze、Daniel E.K. Kabotso、Nicola L.B. Pohl

  DOI：10.1016/j.tetlet.2013.09.014

  日期：2013.12

  An exploration of the role of para-substituents on the balance between stability and reactivity of N-phenyl trifluoroacetimidates prompted the discovery of new reagents for the addition of allyl and benzyl protecting groups, namely O-allyl and O-benzyl N-(p-nitrophenyl)trifluoroimidates. These compounds are stable and crystalline at ambient temperature, making them ideal alternatives to existing benzylating and allylating reagents used under acidic conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.