2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose | 405060-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose
• 英文别名: 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranose；(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-thiol
• CAS: 405060-39-1
• 化学式: C₃₄H₃₆O₅S
• 分子量: 556.723
• InChiKey: LJMMNXCZSYDRSR-BWNLSPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose 在 氨 、 sodium 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 (2R,3R,4S,5R,6R)-2-[10-[diethoxy(oxido)phosphaniumyl]decylsulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  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：

  1-S-thio-(p-nitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-galactopyranose
  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

文献信息

• The Direct Formation of Glycosyl Thiols from Reducing Sugars Allows One-Pot Protein Glycoconjugation
  作者：Gonçalo J. L. Bernardes、David P. Gamblin、Benjamin G. Davis

  DOI：10.1002/anie.200600685

  日期：2006.6.12
• 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.
• 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.