12-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanyldodecan-1-ol | 899430-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanyldodecan-1-ol
• CAS: 899430-10-5
• 化学式: C₄₆H₆₀O₆S
• 分子量: 741.045
• InChiKey: PAPUQCIWGKRSFF-JQIFVRNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  12-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanyldodecan-1-ol 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 12-hydroxydodecyl 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：

  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 12-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanyldodecan-1-ol
  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

• 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.