2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride | 112346-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride
• 英文别名: (2R,3R,4S,5R,6R)-2-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-prop-2-enoxyoxane
• CAS: 112346-23-3
• 化学式: C₃₀H₃₃ClO₅
• 分子量: 509.042
• InChiKey: CXZWUXVOSAYHFF-RLXMVLCYSA-N

物化性质

• 沸点：
  613.9±55.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 在 palladium dichloride molecular sieve 、 4 A molecular sieve 、 sodium methylate 、 sodium acetate 、 silver perchlorate 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 O-(2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyanoside
  参考文献：
  名称：

  曲酒四糖和曲酒五糖的合成

  摘要：

  摘要高氯酸银促进的Koenigs合成了曲二糖[α-d -Glc p-（1→2）-α-d -Glc p-（1→2）-d -Glc p]，曲四糖和曲五戊。 -克诺尔型缩合反应，使用3,4,6-三-O-乙酰基-2-O-烯丙基-β-d-吡喃葡萄糖基氯和七-O-乙酰基-β-曲霉生物基氯作为关键中间体。还描述了α-β-Glcp-（1→2）-α-d-Glc p-（1→3）-d -Glc p的合成。

  DOI：

  10.1016/0008-6215(87)80204-5
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-O-allyl-1-thio-α,β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 1,1-二氯甲醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis

  摘要：

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

  DOI：

  10.1021/jo962300y

文献信息

• CHERNYAK, A. YA.;DEMIDOV, I. V.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 16,(1990) N, S. 537-549
  作者：CHERNYAK, A. YA.、DEMIDOV, I. V.、KOCHETKOV, N. K.

  DOI：——

  日期：——