benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside | 217456-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside
• 英文别名: (3R,4S,5R,6R)-2-benzylsulfonyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 217456-68-3
• 化学式: C₄₁H₄₂O₇S
• 分子量: 678.846
• InChiKey: RVWRBAMWLVDHHG-WWGFXPMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside 在 aluminum oxide 、 氢氧化钾 、 palladium on activated charcoal 、 二溴二氟甲烷 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 、 叔丁醇 为溶剂， 5.0~25.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane
  参考文献：
  名称：

  Benzylic C-glycosides via the Ramberg-Backlund reaction

  摘要：

  Easily prepared thioglycosides are oxidized to the sulfone level and then are subjected to Ramberg-Backlund conditions, i.e. a base plus halogenating agent. The products are exo glycals which upon hydrogenation afford C-glycosides (C) 1998 Elsevier Science Ltd. An rights reserved.

  DOI：

  10.1016/s0040-4039(98)01881-4
• 作为产物：
  描述：

  (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran 在 MMPA 作用下， 以95%的产率得到benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside
  参考文献：
  名称：

  Benzylic C-glycosides via the Ramberg-Backlund reaction

  摘要：

  Easily prepared thioglycosides are oxidized to the sulfone level and then are subjected to Ramberg-Backlund conditions, i.e. a base plus halogenating agent. The products are exo glycals which upon hydrogenation afford C-glycosides (C) 1998 Elsevier Science Ltd. An rights reserved.

  DOI：

  10.1016/s0040-4039(98)01881-4

文献信息

• A New Route toexo-Glycals Using the Ramberg−Bäcklund Rearrangement
  作者：Frank K. Griffin、Duncan E. Paterson、Paul V. Murphy、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1305::aid-ejoc1305>3.0.co;2-0

  日期：2002.4

  A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg−Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了一种通往外糖4的新途径，其中糖基砜3经历了Ramberg-Bäcklund重排的Meyers变体。据报道，衍生自葡萄糖，半乳糖，甘露糖，纤维二糖和核糖的砜转化为二，三和四取代的烯烃。还介绍了此过程的初步机理研究。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• A Ramberg-Bäcklund approach to exo-glycals
  作者：Frank K. Griffin、Paul V. Murphy、Duncan E. Paterson、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(98)01822-x

  日期：1998.10

  A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes. (C) 1998 Elsevier Science Ltd. All rights reserved.