phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-methanesulfonyl-1-thio-α-D-mannopyranoside | 1204197-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-methanesulfonyl-1-thio-α-D-mannopyranoside
• CAS: 1204197-71-6
• 化学式: C₂₇H₂₈O₇S₂
• 分子量: 528.647
• InChiKey: JXDVWSYRNIVMIS-HPRPSTAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-methanesulfonyl-1-thio-α-D-mannopyranoside 、 sodium thiophenolate 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以32%的产率得到phenyl 3-O-benzyl-4,6-O-benzylidene-2-S-phenyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

  摘要：

  Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-alpha-D-glucopyranosides or dithio-1,2-cis-equatorial/axial-beta-D-mannopyranosides by means of S(N)2 type of reactions. Starting from the ethyl-1-thio derivatives intramolecular 1,2-thio-migration took place predominantly. In the case of mannosides both nucleophilic reagents facilitate the formation of 1-SPh- or 1-SEt glycals by elimination. The formation of unsubstituted glycal could also be observed from the ethyl-1-thio derivatives, especially by using PhSNa as a nucleophile. The 1,2-dithio-glycosides are glycosyl donors affording 1,2-trans-2-thio-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.041
• 作为产物：
  描述：

  甲基磺酰氯 、 (2R,4AR,6R,7S,8R,8AR)-8-(苄氧基)-2-苯基-6-(苯硫基)六氢吡喃并[3,2-D][1,3]二氧杂环己烯-7-醇 在 吡啶 作用下， 反应 4.0h， 生成 phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-methanesulfonyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

  摘要：

  Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-alpha-D-glucopyranosides or dithio-1,2-cis-equatorial/axial-beta-D-mannopyranosides by means of S(N)2 type of reactions. Starting from the ethyl-1-thio derivatives intramolecular 1,2-thio-migration took place predominantly. In the case of mannosides both nucleophilic reagents facilitate the formation of 1-SPh- or 1-SEt glycals by elimination. The formation of unsubstituted glycal could also be observed from the ethyl-1-thio derivatives, especially by using PhSNa as a nucleophile. The 1,2-dithio-glycosides are glycosyl donors affording 1,2-trans-2-thio-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.041