methyl 2,3-di-O-benzyl-4-S-[(Z)-2-(phenylsulfonyl)-vinyl]-4-thio-β-D-glucopyranoside | 894428-41-2

• 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-4-S-[(Z)-2-(phenylsulfonyl)-vinyl]-4-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-3-[(Z)-2-(benzenesulfonyl)ethenyl]sulfanyl-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 894428-41-2
• 化学式: C₂₉H₃₂O₇S₂
• 分子量: 556.701
• InChiKey: CTYOOUSHGFJFLI-BYAHAWFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4-S-[(Z)-2-(phenylsulfonyl)-vinyl]-4-thio-β-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80%的产率得到methyl 2,3-di-O-benzyl-6-O,4-S-[(1R)-2-(phenylsulfonyl)-ethylidene]-4-thio-β-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-6-O-benzoyl-β-D-galactopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 methyl 2,3-di-O-benzyl-4-S-[(Z)-2-(phenylsulfonyl)-vinyl]-4-thio-β-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

• Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes
  作者：Florence Chéry、Christelle Pillard、Arnaud Tatibouët、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/j.tet.2006.03.023

  日期：2006.5

  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.