ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 454664-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8S,8aR)-6-ethylsulfanyl-2-phenyl-7-phenylmethoxy-8-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 454664-79-0
• 化学式: C₅₆H₆₀O₁₀S
• 分子量: 925.152
• InChiKey: IQJNDZDLBTZPSD-LMLKWEHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl O-(3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 、 ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以47%的产率得到methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-O-(3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF THE TETRASACCHARIDE Glc α (1→3) Man α (1→2) Man α (1→2) Man α (OMe) AS INHIBITOR OF CALNEXIN BINDING TO GlcMan ₉GlcNAc ₂ ^a

  摘要：

  Tetrasaccharide GlcMan(3) is an inhibitor of GlcMan(9)GlcNAc(2) binding to calnexin, a chaperone protein involved in CFTR-DeltaF 508 retention. A convergent route to its methyl glycoside, the title tetrasaccharide, was developed. The key building block Glc alpha (1-->3) Man 6 was stereoselectively obtained by condensation of a trichloroacetimidate glucosyl donor with an ethyl thiomannopyranoside acceptor. Di-mannose moiety 10 and final compound 12 resulted from thioglycoside activations.

  DOI：

  10.1081/car-120003743
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 sodium hydroxide 、 n-BuNHSO4 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF THE TETRASACCHARIDE Glc α (1→3) Man α (1→2) Man α (1→2) Man α (OMe) AS INHIBITOR OF CALNEXIN BINDING TO GlcMan ₉GlcNAc ₂ ^a

  摘要：

  Tetrasaccharide GlcMan(3) is an inhibitor of GlcMan(9)GlcNAc(2) binding to calnexin, a chaperone protein involved in CFTR-DeltaF 508 retention. A convergent route to its methyl glycoside, the title tetrasaccharide, was developed. The key building block Glc alpha (1-->3) Man 6 was stereoselectively obtained by condensation of a trichloroacetimidate glucosyl donor with an ethyl thiomannopyranoside acceptor. Di-mannose moiety 10 and final compound 12 resulted from thioglycoside activations.

  DOI：

  10.1081/car-120003743

文献信息

• SYNTHESIS OF THE TETRASACCHARIDE Glc α (1→3) Man α (1→2) Man α (1→2) Man α (OMe) AS INHIBITOR OF CALNEXIN BINDING TO GlcMan ₉GlcNAc ₂ ^a
  作者：Slim Cherif、Jean-Marc Clavel、Claude Monneret

  DOI：10.1081/car-120003743

  日期：2002.5.31

  Tetrasaccharide GlcMan(3) is an inhibitor of GlcMan(9)GlcNAc(2) binding to calnexin, a chaperone protein involved in CFTR-DeltaF 508 retention. A convergent route to its methyl glycoside, the title tetrasaccharide, was developed. The key building block Glc alpha (1-->3) Man 6 was stereoselectively obtained by condensation of a trichloroacetimidate glucosyl donor with an ethyl thiomannopyranoside acceptor. Di-mannose moiety 10 and final compound 12 resulted from thioglycoside activations.