Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside | 151123-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside
• CAS: 151123-92-1
• 化学式: C₁₅H₂₀O₅S
• 分子量: 312.387
• InChiKey: QOMMDHDGIYADCQ-CVRPCMMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 三乙胺 、 硫脲 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3–8

  摘要：

  Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1 --> 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1 --> 3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1 --> 3)-linked beta-D-gluco-Oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80061-i
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 四氯化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、4.0 kPa 条件下， 反应 21.0h， 生成 Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3–8

  摘要：

  Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1 --> 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1 --> 3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1 --> 3)-linked beta-D-gluco-Oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80061-i