ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside | 218937-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
• CAS: 218937-72-5
• 化学式: C₃₀H₃₄O₆S
• 分子量: 522.662
• InChiKey: PXBWIWBRWZVTGN-RTJSNJMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 18.0h， 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
• 作为产物：
  描述：

  4-甲氧基氯苄 在 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-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

• Influence of remote functional groups towards the formation of 1,2-<i>cis</i> glycosides: special emphasis on β-mannosylation
  作者：Arin Gucchait、Anup Kumar Misra

  DOI：10.1039/c9ob00670b

  日期：——

  The influence of remote functional groups for the stereoselective formation of 1,2-cis glycosides and β-mannosides is reported.

  远程官能团对1,2-cis葡萄糖苷和β-甘露苷的立体选择性形成的影响已被报道。