methyl 2,3-di-O-benzyl-6-thio-α-D-glucopyranoside | 604757-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-thio-α-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(sulfanylmethyl)oxan-3-ol
• CAS: 604757-18-8
• 化学式: C₂₁H₂₆O₅S
• 分子量: 390.5
• InChiKey: JNKKDOIEEGQPDD-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-thio-α-D-glucopyranoside 在 正丁基锂 、 四丁基溴化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 methyl 2,3-di-O-benzyl-6-S-[(E)-2-(phenylsulfonyl)-vinyl]-6-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：

  2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.0h， 生成 methyl 2,3-di-O-benzyl-6-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

• Expeditious synthesis of β-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent
  作者：Elena Cabianca、Arnaud Tatibouët、Fabrizio Fabris、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/j.tetlet.2004.11.151

  日期：2005.2

  In similarity with the strongly electrophilic BPSEs and despite its more electron-rich character, 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) reacts with nucleophiles with displacement of the phenylthio moiety. Specifically it reacts with diols under basic conditions to produce beta-cycloacetalic sulfoxides. The reaction has been amply developed in carbohydrate chemistry. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• 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.