1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside | 405060-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
• 英文别名: 1-S-p-nitrobenzoyl-2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranose；S-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 4-nitrobenzenecarbothioate
• CAS: 405060-38-0
• 化学式: C₄₁H₃₉NO₈S
• 分子量: 705.829
• InChiKey: UIXYLTITTQGTLW-QHVMBNAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 在 sodium methylate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 10-hydroxydecyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside
  参考文献：
  名称：

  Unusual anomeric rearrangement of para-nitrobenzoylxanthate d-glycosides: a new direct stereoselective access to α-thioglycosides from pyranose sugars

  摘要：

  A mild and general procedure for the synthesis of alpha-thioglycosides from glycopyranoses is described. The method involves the treatment of pyranose reductive sugar with sodium hydride, carbon disulfide, and p-nitrobenzoyl chloride, as a key step, to yield p-nitrobenzoyl-alpha-D-thioglycopyranose intermediates with high stereoselectivity, in a one-pot-two-step process. The interest of the strategy highlights a direct stereoselective access to ether-protected 1-thiol-alpha-D-glycopyranose derivatives (Gal, Glc, and Man) from pyranoses in the absence of anomeric 'Lewis acid' promoters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.024
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-吡喃半乳糖 在 咪唑 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 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

文献信息

• Unusual anomeric rearrangement of para-nitrobenzoylxanthate d-glycosides: a new direct stereoselective access to α-thioglycosides from pyranose sugars
  作者：Adjou Ané、Solen Josse、Sébastien Naud、Vivien Lacône、Sandrine Vidot、Anaïs Fournial、Anirban Kar、Muriel Pipelier、Didier Dubreuil

  DOI：10.1016/j.tet.2006.03.024

  日期：2006.5

  A mild and general procedure for the synthesis of alpha-thioglycosides from glycopyranoses is described. The method involves the treatment of pyranose reductive sugar with sodium hydride, carbon disulfide, and p-nitrobenzoyl chloride, as a key step, to yield p-nitrobenzoyl-alpha-D-thioglycopyranose intermediates with high stereoselectivity, in a one-pot-two-step process. The interest of the strategy highlights a direct stereoselective access to ether-protected 1-thiol-alpha-D-glycopyranose derivatives (Gal, Glc, and Man) from pyranoses in the absence of anomeric 'Lewis acid' promoters. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.