methyl O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 192936-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: [(2R,4aR,6R,7S,8S,8aR)-6-[[(2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy]-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] acetate
• CAS: 192936-02-0
• 化学式: C₄₃H₄₆O₁₂
• 分子量: 754.831
• InChiKey: CCQHICAUDRWTSJ-GXUCKMSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到methyl 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：

  (2R,4AR,6R,7S,8R,8AR)-8-(苄氧基)-2-苯基-6-(苯硫基)六氢吡喃并[3,2-D][1,3]二氧杂环己烯-7-醇 在 吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 methyl O-(2-O-acetyl-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

文献信息

• Misra, Anup Kumar; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 4, p. 308 - 311
  作者：Misra, Anup Kumar、Roy, Nirmolendu

  DOI：——

  日期：——