methyl (carboxymethyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 1159257-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (carboxymethyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: 2-[(2R,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-methoxy-1,3-bis(phenylmethoxy)propyl]-2-methoxycarbonyl-4-phenylmethoxyoxan-2-yl]oxyacetic acid
• CAS: 1159257-93-8
• 化学式: C₃₆H₄₃NO₁₁
• 分子量: 665.738
• InChiKey: GUZSXHWKKGWGPC-VLVHFTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (carboxymethyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate 、 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-amino-D-glycero-α-D-galacto-2-nonulopyranosylonate)-2-(2->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以57%的产率得到2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,9-tri-O-benzyl-8-O-methyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->11)-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-glycolylamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the starfish ganglioside LLG-3 tetrasaccharide

  摘要：

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.003
• 作为产物：
  描述：

  methyl (benzyloxycarbonylmethyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到methyl (carboxymethyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of the starfish ganglioside LLG-3 tetrasaccharide

  摘要：

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.003

文献信息

• Synthesis of the starfish ganglioside LLG-3 tetrasaccharide
  作者：Shinya Hanashima、Daichi Ishikawa、Shoji Akai、Ken-ichi Sato

  DOI：10.1016/j.carres.2009.02.003

  日期：2009.4

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.