(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran | 217456-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran
• 英文别名: (3R,4S,5R,6R)-2-benzylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 217456-63-8
• 化学式: C₄₁H₄₂O₅S
• 分子量: 646.847
• InChiKey: LPGXUYMYRDMAFA-WWGFXPMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  47
• 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：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran 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：

  甲基 2,3,4,6-O-四苄基-alpha-D-吡喃葡萄糖苷 在 三甲基氯硅烷 、 硫酸 、 zinc trifluoromethanesulfonate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran
  参考文献：
  名称：

  A Ramberg-Bäcklund approach to exo-glycals

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)01822-x

文献信息

• Removal of Benzyl Protecting Groups from Solid-Supported Compounds by Hydrogenolysis Using Palladium Nanoparticles
  作者：Osamu Kanie、Gijsbert Grotenbreg、Chi-Huey Wong

  DOI：10.1002/1521-3773(20001215)39:24<4545::aid-anie4545>3.0.co;2-v

  日期：2000.12.15
• 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.
• Benzylic C-glycosides via the Ramberg-Backlund reaction
  作者：Peter S. Belica、Richard W. Franck

  DOI：10.1016/s0040-4039(98)01881-4

  日期：1998.11

  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.