methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside | 58341-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-prop-2-enoxyoxane
• CAS: 58341-63-2
• 化学式: C₃₁H₃₆O₆
• 分子量: 504.623
• InChiKey: ICDZPHNZHXNRPD-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以72%的产率得到2-O-allyl-3,4,6-tri-O-benzyl-D-glucopyranose
  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：

  methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and stereochemical confirmation of the cis-fused L/M and N/O ring systems of maitotoxin

  摘要：

  Stereocontrolled synthesis of cis-fused 1,6-dioxadecalin system 1, which corresponds to the L/M and N/O rings of maitotoxin, was accomplished. Comparison of its H-1 and C-13 NMR data with those of the natural toxin established the earlier stereochemical assignments.

  DOI：

  10.1016/s0040-4039(00)73310-7

文献信息

• Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis
  作者：Vince Pozsgay、Eric P. Dubois、Lewis Pannell

  DOI：10.1021/jo962300y

  日期：1997.5.1

  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.
• 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：——