allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside | 518975-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside
• CAS: 518975-23-0
• 化学式: C₅₂H₄₈O₁₆
• 分子量: 928.944
• InChiKey: JGQGOAZITQGPHZ-WNKCOHIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  68.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF β-d-Glcp-(1→2)-[β-d-Ribf-(1→3)-]α-l-Rhap-(1→3)-α-l-Rhap-(1→2)-α-l-Rhap, THE REPEATING UNIT OF THE LIPOPOLYSACCHARIDE OF Acetobacter diazotrophicus PAL 5

  摘要：

  A pentasaccharide, the major repeating unit of the lipopolysaccharide (LPS) of the nitrogen fixing bacterium Acetobacter diazotrophicus PAL 5 was efficiently synthesized as its allyl glycoside using a regio- and stereoselective strategy. The key acceptor, allyl 3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranoside (3), was prepared by selective 3-O-acetylation of allyl 4-O-benzoyl-alpha-L-rhamnopyranoside. Condensation of 3 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate furnished the disaccharide 5. Deallylation and subsequent trichloroacetimidation of 5 afforded 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 2)-3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (10). Selective 3-O-glycosylation of allyl alpha-L-rhamnopyranoside (1) with 10 followed by benzoylation gave trisaccharide (12), which could be conveniently converted to a donor (14). Condensation of 14 with allyl 3,4-di-O-benzoyl-alpha-L-rhamnopyranoside (15) gave tetrasaccharide, 16. Selective deacetylation of 16 gave the acceptor 17 which was ribosylated to furnish the protected pentasaccharide, and finally deprotection led to the title compound.

  DOI：

  10.1081/car-120016856
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 、 allyl 3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84.5%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF β-d-Glcp-(1→2)-[β-d-Ribf-(1→3)-]α-l-Rhap-(1→3)-α-l-Rhap-(1→2)-α-l-Rhap, THE REPEATING UNIT OF THE LIPOPOLYSACCHARIDE OF Acetobacter diazotrophicus PAL 5

  摘要：

  A pentasaccharide, the major repeating unit of the lipopolysaccharide (LPS) of the nitrogen fixing bacterium Acetobacter diazotrophicus PAL 5 was efficiently synthesized as its allyl glycoside using a regio- and stereoselective strategy. The key acceptor, allyl 3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranoside (3), was prepared by selective 3-O-acetylation of allyl 4-O-benzoyl-alpha-L-rhamnopyranoside. Condensation of 3 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate furnished the disaccharide 5. Deallylation and subsequent trichloroacetimidation of 5 afforded 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 2)-3-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (10). Selective 3-O-glycosylation of allyl alpha-L-rhamnopyranoside (1) with 10 followed by benzoylation gave trisaccharide (12), which could be conveniently converted to a donor (14). Condensation of 14 with allyl 3,4-di-O-benzoyl-alpha-L-rhamnopyranoside (15) gave tetrasaccharide, 16. Selective deacetylation of 16 gave the acceptor 17 which was ribosylated to furnish the protected pentasaccharide, and finally deprotection led to the title compound.

  DOI：

  10.1081/car-120016856