3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate | 86032-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate
• CAS: 86032-57-7
• 化学式: C₂₈H₃₄O₇
• 分子量: 482.574
• InChiKey: QFFLLQRZQWZLTI-MASCHLQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl p-nitrobenzoate
  参考文献：
  名称：

  保护的三己糖基单元的合成：对应于糖蛋白N-连接聚糖核心结构的糖基受体。

  摘要：

  DOI：

  10.1016/0008-6215(83)88397-9
• 作为产物：
  描述：

  methyl 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside 、 乙酸酐 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以79.1%的产率得到3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl acetate
  参考文献：
  名称：

  糖蛋白复杂类型的聚糖链的六糖单元的合成。

  摘要：

  DOI：

  10.1016/0008-6215(83)88189-0

文献信息

• Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein
  作者：Fumito Yamazaki、Tohru Kitajima、Tomoo Nukada、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(90)84222-g

  日期：1990.6

  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.
• A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane-1,2-diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide
  作者：Peter Grice、Steven V. Ley、Jörg Pietruszka、Helen M. I. Osborn、Henning W. M. Priepke、Stuart L. Warriner

  DOI：10.1002/chem.19970030315

  日期：——

  AbstractThe high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.