methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside | 130257-50-0

• 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-tert-butyldimethylsilyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 130257-50-0
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: AEYPGYBPBJVRON-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 重铬酸吡啶 、 氢气 、 硼酸 、 三甲基铵三氧化硫共聚物 、 nickel dichloride 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-β-D-galactopyranosyl)-β-D-glucopyranosiduronic acid, disodium salt
  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：

  甲基 Β-D-吡喃葡萄糖苷 在 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  O-Sulfated Derivatives of Glucuronic Acid

  摘要：

  为了研究硫酸化的区域选择性，我们以 D-葡萄糖为原料合成了 4-O-取代的 D-葡萄糖醛酸衍生物。

  DOI：

  10.3390/50300600

文献信息

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

  DOI：——

  日期：——