4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide | 129354-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide
• CAS: 129354-11-6
• 化学式: C₄₃H₅₃BrO₆Si₂
• 分子量: 801.965
• InChiKey: ZPRVLPUDCMEGBX-HJRBIJKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide 、 allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside 在 silver silicate 、 4 A molecular sieve 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以60%的产率得到allyl O-(4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g
• 作为产物：
  描述：

  2,2,2-trichloroethyl 3-O-tert-butyldiphenylsilyl-4,6-O-isopropylidene-α-D-mannopyranoside 在 吡啶 、 咪唑 、 氢溴酸 、 四丁基碘化铵 、 potassium hydride 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.33h， 生成 4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g