2,3,4-tri-O-benzyl-D-glucitol | 187103-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4-tri-O-benzyl-D-glucitol
• 英文别名: (2R,3R,4R,5S)-3,4,5-tris(phenylmethoxy)hexane-1,2,6-triol
• CAS: 187103-77-1
• 化学式: C₂₇H₃₂O₆
• 分子量: 452.547
• InChiKey: VEVLEKXTJKDJAO-HVWQDESWSA-N

物化性质

• 沸点：
  644.3±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-D-glucitol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 camphor-10-sulfonic acid 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.33h， 生成 1-O-acetyl-5-azido-2,3,4-tri-O-benzyl-6-O-t-butyldiphenylsilyl-5-deoxy-D-iditol
  参考文献：
  名称：

  Synthesis of the Dimethyl Ester of 1‐Deoxy‐l‐Idonojirimycin‐1‐Methylenphosphonate: A New Approach to Iminosugar Phosphonates

  摘要：

  1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12.[GRAPHICS]

  DOI：

  10.1080/07328300600731990
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-glucopyranose 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-benzyl-D-glucitol
  参考文献：
  名称：

  Synthesis of the Dimethyl Ester of 1‐Deoxy‐l‐Idonojirimycin‐1‐Methylenphosphonate: A New Approach to Iminosugar Phosphonates

  摘要：

  1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12.[GRAPHICS]

  DOI：

  10.1080/07328300600731990

文献信息

• Stereoselective Synthesis of Branched Cyclopentitols by Titanium(III)-Promoted Reductive Cyclization of 4-Oxiranylaldehydes and 4-Oxiranyl Ketones Derived from Hexoses
  作者：Jose Chiara、Sofía Bobo、Esther Sesmilo

  DOI：10.1055/s-2008-1067257

  日期：2008.10

  Titanocene chloride efficiently promotes the intramolecular reductive cross coupling of highly functionalized 4-oxiranyl-aldehydes and 4-oxiranyl ketones derived from readily available hexoses affording branched cyclopentitols with good stereoselectivity.

  氯化二茂钛有效地促进了高度官能化的 4-环氧乙烷基醛和 4-环氧乙烷基酮的分子内还原交叉偶联，这些酮衍生自容易获得的己糖，从而提供具有良好立体选择性的支链环戊糖醇。
• Optimized synthesis of a pentafluoro- gem -diol and conversion to a CF2Br -glucopyranose through trifluoroacetate-release and halogenation
  作者：Robert A. Hazlitt、Jinu P. John、Que-Lynn Tran、David A. Colby

  DOI：10.1016/j.tetlet.2016.03.064

  日期：2016.4

  enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors. Herein, two new synthetic strategies to a complex pentafluoro-gem-diol are compared to the existing route, and an improved synthetic route has completed. Moreover, the first synthesis of a CF2Br-glucopyranose

  五氟宝石二醇是能够通过释放三氟乙酸盐来合成有价值的含二氟亚甲基有机分子的底物。当前，只有一种合成策略可用于组装这些重要的前体。在本文中，将两种新的合成五氟-宝石-二醇的合成策略与现有路线进行了比较，并完成了一种改进的合成路线。此外，通过串联释放三氟乙酸盐的卤化/环化方案完成了CF2Br-吡喃葡萄糖的首次合成。
• The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols
  作者：Mykhaylo A. Potopnyk、Piotr Cmoch、Maciej Cieplak、Agnieszka Gajewska、Sławomir Jarosz

  DOI：10.1016/j.tetasy.2011.04.021

  日期：2011.4

  The C12 higher sugar enone 15 (prepared from the corresponding phosphonate and aldehyde) was highly stereoselectively reduced to the D-glycero-allylic alcohol. The epimeric L-glycero-isomer was obtained by the non-selective reduction of the higher enone under Luche conditions. The separate treatment of both allylic alcohols with triflic anhydride provided the corresponding triflates, which in situ underwent allylic rearrangement with the elimination of one of the benzyl groups (from the aldehyde part of the molecule). The stereochemical aspects of this transformation are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.