ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 383190-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Glc6Ac(a1-3)[Bn(-2)][Bn(-4)]Rha(a)-SEt；[(2R,3R,4S,5R,6R)-6-[(2S,3R,4R,5S,6S)-2-ethylsulfanyl-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 383190-12-3
• 化学式: C₅₁H₅₈O₁₀S
• 分子量: 863.082
• InChiKey: CDMKYBGZEVRWRI-NWSDSDQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside 、 ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 0.17h， 以65.5%的产率得到benzyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the α-d-GlcpA-(1→3)-α-l-Rhap-(1→2)-l-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

  摘要：

  The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha -D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha -L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6 " -OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00196-3
• 作为产物：
  描述：

  ethyl 4-O-benzyl-2,3-O-benzylidene-1-thio-α-L-rhamnopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 ethyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the α-d-GlcpA-(1→3)-α-l-Rhap-(1→2)-l-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

  摘要：

  The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha -D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha -L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6 " -OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00196-3