methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside | 156660-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside
• CAS: 156660-50-3
• 化学式: C₄₁H₄₈O₁₀
• 分子量: 700.826
• InChiKey: DKFILHOMIPMYMO-CCYJPFHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  114.3
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside 在 sodium hydroxide 、 4 A molecular sieve 、 四丁基溴化铵 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 85.0h， 生成 methyl 3-O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-2-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  与55型克雷伯菌的抗原重复单元有关的四糖的合成。

  摘要：

  DOI：

  10.1016/0008-6215(94)80077-4
• 作为产物：
  描述：

  methyl 4-O-β-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranoside
  参考文献：
  名称：

  与55型克雷伯菌的抗原重复单元有关的四糖的合成。

  摘要：

  DOI：

  10.1016/0008-6215(94)80077-4

文献信息

• Synthesis of the Methyl Glycosides of a Di- and Two Trisaccharide Fragments Specific for the<i>Shigella flexneri</i>Serotype 2a<i>O</i>-Antigen
  作者：Laurence A. Mulard、Corina Costachel、Philippe J. Sansonetti

  DOI：10.1080/07328300008544123

  日期：2000.1

  The stereocontrolled synthesis of methyl alpha-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranoside (EC, 1), methyl alpha-L-rhamnopyranosyl-(1-->3)-[alpha-D-glucopyra- osyl-(1-->4)]-alpha-L-rhamnopyranoside (B(E)C, 3) and methyl alpha-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (ECD, 4) is described; these constitute the methyl glycosides of branched and linear fragments of the O-specific polysaccharide of Shigella flexneri serotype 2a. Emphasis was put on the construction of the 1,2-cis EC glycosidic linkage resulting in the selection of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride (8) as the donor. Condensation of methyl 2,3-O-isopropylidene-4-O-trimethylsilyloside-alpha-L-rhamnopyranoside (11) and 8 afforded the fully protected alpha E-disaccharide 20, as a common intermediate in the synthesis of 1 and 3, together with the corresponding beta E-anomer 21. Deacetalation and regioselective benzoylation of 20, followed by glycosylation with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (15) afforded the branched trisaccharide 25. Full deprotection of 20 and 25 afforded the targets 1 and 3, respectively. The corresponding beta E-disaccharide, namely, methyl beta-D-glucopyranosyl-(1-->4)-a-L-rhamnopyranoside (PEC, 2) was prepared analogously from 21. Two routes to trisaccharide 4 were considered. Route 1 involved the coupling of a precursor to residue E and a disaccharide CD. Route 2 was based on the condensation of an appropriate EC donor and a precursor to residue D. The former route afforded a 1:2 mixture of the alpha E and PE condensation products which could not be separated, neither at this stage, nor after deacetalation. In route 2, the required alpha E-anomer was isolated at the disaccharide stage and transformed into 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl-(1-->4)-2,3-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (48) as the EC donor. Methyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyran-oside (19) was preferred to its benzylidene analogue as the precursor to residue D. Condensation of 19 and 48 and stepwise deprotection of the glycosylation product afforded the target 4.
• Das, Saibal Kumar; Roy, Nirmolendu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 417 - 428
  作者：Das, Saibal Kumar、Roy, Nirmolendu

  DOI：——

  日期：——