phenyl 3-O-benzyl-4,6-O-benzylidene-2-S-ethyl-1-thio-α-D-glucopyranoside | 1204197-82-9

• 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-S-ethyl-1-thio-α-D-glucopyranoside
• CAS: 1204197-82-9
• 化学式: C₂₈H₃₀O₄S₂
• 分子量: 494.676
• InChiKey: CFKXDXQMHRLXFE-XXDTVXIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 phenyl 3-O-benzyl-4,6-O-benzylidene-2-S-ethyl-1-thio-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以72%的产率得到methyl 3-O-benzyl-4,6-O-benzylidene-2-S-ethyl-β-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：

  ethyl 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28%的产率得到1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol
  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