methyl 2,3-di-O-benzyl-6-O-chloroacetyl-β-D-glucopyranoside | 130257-49-7

• 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-O-chloroacetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-chloroacetate
• CAS: 130257-49-7
• 化学式: C₂₃H₂₇ClO₇
• 分子量: 450.916
• InChiKey: ISHLCKNFOOKHKC-DODNOZFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-O-chloroacetyl-β-D-glucopyranoside 在 吡啶 、 重铬酸吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 47.5h， 生成 methyl (2S,3S,4S,5R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-acetyloxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-acetyloxy-4,5-bis(phenylmethoxy)oxane-2-carboxylate
  参考文献：
  名称：

  Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate

  摘要：

  3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.

  DOI：

  10.1016/0008-6215(90)84259-w
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-β-D-glucopyranoside 在 对甲苯磺酸 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 1.17h， 生成 methyl 2,3-di-O-benzyl-6-O-chloroacetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Acidic Opening of Chlorinated Carbohydrate Orthoacetates

  摘要：

  DOI：

  10.1080/07328309608005670

文献信息

• JACQUINET, JEAN-CLAUDE, CARBOHYDR. RES., 199,(1990) N, C. 153-181
  作者：JACQUINET, JEAN-CLAUDE

  DOI：——

  日期：——