methyl 2,3-di-O-benzyl-6-O,4-S-[(1R)-2-(phenylsulfonyl)-ethylidene]-4-thio-α-D-glucopyranoside | 604757-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-di-O-benzyl-6-O,4-S-[(1R)-2-(phenylsulfonyl)-ethylidene]-4-thio-α-D-glucopyranoside
• CAS: 604757-21-3
• 化学式: C₂₉H₃₂O₇S₂
• 分子量: 556.701
• InChiKey: XMPGKVFAZUAXQJ-AFOZROKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-O,4-S-[(1R)-2-(phenylsulfonyl)-ethylidene]-4-thio-α-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以77%的产率得到methyl 2,3-di-O-benzyl-4-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes

  摘要：

  Based on the vinyl biS-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsul fonyl vinyl sulfides, which have a synthetic potential of their own, emphasizes the versatility of the method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.023
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4-S-[(E)-2-(phenylsulfonyl)-vinyl]-4-thio-α-D-glucopyranoside 在 四丁基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以83%的产率得到methyl 2,3-di-O-benzyl-6-O,4-S-[(1R)-2-(phenylsulfonyl)-ethylidene]-4-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes

  摘要：

  Based on the vinyl biS-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsul fonyl vinyl sulfides, which have a synthetic potential of their own, emphasizes the versatility of the method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.023

文献信息

• Investigating thio-analogues of PSE acetals: a more complex reaction
  作者：Elena Cabianca、Arnaud Tatibouët、Florence Chéry、Christelle Pillard、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/s0040-4039(03)01303-0

  日期：2003.7

  The reaction of hydroxylated thiols with 1,2-bis-phenylsulfonylethylene was investigated: in contrast with diols, a more complex reaction was observed and application to carbohydrate-derived PSE oxathianes was envisaged. (C) 2003 Elsevier Ltd. All rights reserved.