O-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] (4-nitrobenzoyl)sulfanylmethanethioate | 405060-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] (4-nitrobenzoyl)sulfanylmethanethioate
• CAS: 405060-36-8
• 化学式: C₄₂H₃₉NO₉S₂
• 分子量: 765.905
• InChiKey: DCNVSLNAXCHYEH-FXWJQBGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] (4-nitrobenzoyl)sulfanylmethanethioate 在 咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以70%的产率得到1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Rearrangement of 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside: a novel access to α-thioglycoside derivatives

  摘要：

  The synthesis of galactosides thiolate and thioester is described by direct S-glycosylation process from 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside. Three novel anomeric groups are presented as potent glycoside activators: O-(thio-p-nitrobenzoyl)thiocarbonyl, O-(imidazolyl)thiocarbonyl and S.-thio-p-nitrobenzoyl. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02122-0
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-吡喃半乳糖 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 O-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] (4-nitrobenzoyl)sulfanylmethanethioate
  参考文献：
  名称：

  Rearrangement of 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside: a novel access to α-thioglycoside derivatives

  摘要：

  The synthesis of galactosides thiolate and thioester is described by direct S-glycosylation process from 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside. Three novel anomeric groups are presented as potent glycoside activators: O-(thio-p-nitrobenzoyl)thiocarbonyl, O-(imidazolyl)thiocarbonyl and S.-thio-p-nitrobenzoyl. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02122-0

文献信息

• Rearrangement of 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside: a novel access to α-thioglycoside derivatives
  作者：Solen Josse、Julien Le Gal、Muriel Pipelier、Jeannine Cléophax、Alain Olesker、Jean-Paul Pradère、Didier Dubreuil

  DOI：10.1016/s0040-4039(01)02122-0

  日期：2002.1

  The synthesis of galactosides thiolate and thioester is described by direct S-glycosylation process from 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside. Three novel anomeric groups are presented as potent glycoside activators: O-(thio-p-nitrobenzoyl)thiocarbonyl, O-(imidazolyl)thiocarbonyl and S.-thio-p-nitrobenzoyl. (C) 2002 Elsevier Science Ltd. All rights reserved.