2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile | 95084-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile
• 英文别名: 2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetonitrile
• CAS: 95084-03-0
• 化学式: C₃₆H₃₇NO₅
• 分子量: 563.693
• InChiKey: QAYGVXKANOLPDZ-LPMXJBPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile 在 甲醇 、 magnesium 作用下， 反应 18.0h， 以70%的产率得到2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile
  参考文献：
  名称：

  A Mitsunobu route to C-glycosides

  摘要：

  C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach toward the synthesis of C-glycolipids is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.024

文献信息

• Reactions of glycosyl fluorides. Synthesis of C-glycosides
  作者：K. C. Nicolaou、Roland E. Dolle、Alexander Chucholowski、Jared L. Randall

  DOI：10.1039/c39840001153

  日期：——

  Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.

  发现糖基氟化物在催化作用或不催化作用下与许多亲核试剂反应，从而导致多种C-糖苷和相关化合物。
• A convenient synthesis of both the anomers of ethyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)acetate
  作者：Diego Monti、Paola Gramatica、Giovanna Speranza、Paolo Manitto

  DOI：10.1016/s0040-4039(00)96692-9

  日期：1987.1

  The α- and β-anomers of ethyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl) acetate, useful intermediates for the synthesis of alkyl C-glucosides, can be obtained in good yields by reaction of tetra-O-benzylglucose with triethyl phosphonoacetate according to the Wittig-Horner procedure.

  乙酸乙酯（2,3,4,6-四-O-苄基-D-吡喃葡萄糖基）的α-和β-异头物是合成烷基C-葡糖苷的有用中间体，可通过以下反应获得高收率：根据Wittig-Horner程序，用膦酰基乙酸三乙酯合成四-O-苄基葡萄糖。