(2'S,3'S)-ethyl 3-O,4-O-[2',3'-dimethoxybutan-2',3'diyl]-6-O-acetyl-1-thio-α-D-mannopyranoside | 1132975-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,3'S)-ethyl 3-O,4-O-[2',3'-dimethoxybutan-2',3'diyl]-6-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2S,3S,4aR,5R,7R,8S,8aR)-7-ethylsulfanyl-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]methyl acetate
• CAS: 1132975-36-0
• 化学式: C₁₆H₂₈O₈S
• 分子量: 380.46
• InChiKey: NTLIEWSNXWGWCP-ZAJFYCSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2'S,3'S)-ethyl 3-O,4-O-[2',3'-dimethoxybutan-2',3'diyl]-6-O-acetyl-1-thio-α-D-mannopyranoside 、 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到(2'S,3'S)-ethyl 3-O,4-O-[2',3'-dimethoxybutan-2',3'-diyl]-6-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j
• 作为产物：
  描述：

  乙酸酐 、 (2'S,3'S) ethyl 3-O-,4-O-[2',3'-dimethoxybutan-2',3'-diyl]-1-thio-α-D-mannopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到(2'S,3'S)-ethyl 3-O,4-O-[2',3'-dimethoxybutan-2',3'diyl]-6-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j