Methyl 3,6-di-O-benzyl-β-D-glucopyranoside | 158991-97-0

• 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-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxane-3,5-diol
• CAS: 158991-97-0
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: RLGKEERGCGWMKK-SSSFQFABSA-N

物化性质

• 沸点：
  549.3±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3,6-di-O-benzyl-β-D-glucopyranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以41%的产率得到2,5-anhydro-3,6-di-O-benzyl-4-deoxy-1,4-difluoro-1-O-methyl-D-talitol
  参考文献：
  名称：

  Fluorination of 2-hydroxy-hexopyranosides by DAST: towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides

  摘要：

  Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-I-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. F-19/H-1 and F-19/C-13 coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O-methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.034
• 作为产物：
  描述：

  溴甲苯 、 甲基 Β-D-吡喃葡萄糖苷 在 二正丁基氧化锡 作用下， 生成 Methyl 3,6-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Qin, Huiping; Grindley, T. Bruce, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 3, p. 475 - 490

  摘要：

  DOI：