Methyl 2-O-(β-D-glucopyranosyl)-3-O-(β-L-fucopyranosyl)-α-L-rhamnopyranoside | 73113-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-O-(β-D-glucopyranosyl)-3-O-(β-L-fucopyranosyl)-α-L-rhamnopyranoside
• 英文别名: Methyl 3-O-(β-L-fucopyranosyl)-2-O-(α-D-mannopyranosyl)-α-L-rhamnopyranoside；methyl O-α-D-glucopyranosyl-(1<*>2)-O-<α-L-rhamnopyranosyl-(1<*>3)>-α-L-rhamnopyranoside；Methyl 2-O-(α-D-mannopyranosyl)-3-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranoside；methyl O-β-D-glucopyranosyl-(1<*>2)-O-<α-L-rhamnopyranosyl-(1<*>3)>-α-L-rhamnopyranoside；Methyl 2-O-(β-D-glucopyranosyl)-3-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• CAS: 73113-85-6；73174-65-9；137493-05-1；137493-10-8；137493-11-9；137493-13-1；137767-23-8
• 化学式: C₁₉H₃₄O₁₄
• 分子量: 486.471
• InChiKey: KFYOGMHHIJCJSF-XPHNVMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.86
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  217.22
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以82%的产率得到Methyl 2-O-(β-D-glucopyranosyl)-3-O-(β-L-fucopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of di-O-glycosyl derivatives of methyl α-l-rhamnopyranoside

  摘要：

  The syntheses are described of 2,3-di-O-glycosyl derivatives (1-12) of methyl alpha-L-rhamnopyranoside where the glycosyl moieties are variously alpha-L-fucopyranose, beta-L-fucopyranose, beta-D-glucopyranose, alpha-D-mannopyranose, and alpha-L-rhamnopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-alpha-L-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-alpha-L-rhamnopyranoside (25), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside (29), methyl 4-O-benzoyl-3-O-(2, 3,4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3, 4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (59). In the syntheses of compounds 7-9, the alpha-L-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-alpha-L-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-l-thio-beta-L-fucopyranoside (47) as glycosyl donors.

  DOI：

  10.1016/0008-6215(92)80010-x

文献信息

• Synthesis of part of the antigenic repeating-unit of streptococcus pneumoniae type II
  作者：Dominique Schwarzenbach、Roger W. Jeanloz

  DOI：10.1016/s0008-6215(00)85919-4

  日期：1981.4

  Abstract Condensation of methyl 4- O -acetyl-3- O -(2,3,4-tri- O -acetyl-α- l -rhamnopyranosyl)-α- l -rhamnopyranoside with 2,3,4,6-tetra- O -benzyl-α- d -glucopyranosyl chloride gave a mixture of methyl O -[2,3,4,6-tetra- O -benzyl-α- ( 4 ) and -β- d -glucopyranosyl]-(1→2)- O -[(2,3,4-tri- O -acetyl-α- l -rhamnopyranosyl)-(1→3)]-4- O -acetyl-α- l -rhamnopyranoside ( 9 ) in 43:7 proportion in 63% yield

  摘要4- O-乙酰-3- O-（2,3,4-三-O-乙酰-α-l-鼠李糖吡喃糖基）-α-l-鼠李糖吡喃糖苷与2,3,4,6-四- O-苄基-α-d-吡喃葡萄糖基氯得到甲基O- [2,3,4,6-四-O-苄基-α-（4）和-β-d-吡喃葡萄糖基]-（1→2的混合物）-O-[（2,3,4-三-O-乙酰基-α-1-鼠李糖吡喃糖基）-（1→3）]-4-O-乙酰基-α-1-鼠李糖吡喃糖苷（9）in 43：7比例为63％的收率。色谱分离后，除去苄基和乙酰基，得到甲基O-α-d-吡喃葡萄糖基-（1→2）-[O-α-1-rhamnopyranosyl-（1→3）]-α-1-r-rhamnopyranoside和β端基异构体。除去4的苄基，然后进行α-d-吡喃葡萄糖基的三苯甲基化，乙酰化和去三苯甲基化，最后与苄基（2,3，4-三-O-苄基-d-吡喃葡萄糖基氯）脲酸酯得到两种四糖（15和16）的混合物，包含比