Methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-bis3)>-2,4,6-tri-O-acetyl-β-D-glucopyranoside | 151072-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-bis3)>-2,4,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: methyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 151072-73-0
• 化学式: C₅₁H₇₀O₃₄
• 分子量: 1227.1
• InChiKey: LFULILZBBUBHRD-WQSWTTOKSA-N

物化性质

• 沸点：
  992.3±65.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 重原子数：
  85.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  415.74
• 氢给体数：
  0.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  Methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-bis3)>-2,4,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到methyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3–8

  摘要：

  Ethyl 2,3,4,6-tetra-O-acetyl-l-thio-alpha-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding beta-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-alpha-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a beta-(1 --> 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a beta-(1 --> 3)-linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 3)-2-O-benzoyl-4,6-O-benzylidene-beta-D-glucopyranoside (26). The methyl beta-glycosides of a homologous series of (1 --> 3)-linked beta-D-gluco-Oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80061-i
• 作为产物：
  描述：

  乙酸酐 、 methyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 生成 Methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-bis3)>-2,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  通过使用来自大麦的突变的（1,3）-β-D-葡聚糖内切酶合成复杂的寡糖。

  摘要：

  当取代或未取代的α-laminaribiosyl氟化物，作为供体，通过缩合生成单糖和二糖β-D-己基吡喃糖苷受体时，可以良好的产率获得具有新形成的（1,3）-β-糖苷键的复杂寡糖。 （1,3）-β-D-糖基合成酶。这些线性和分支的（1,3）-β-连接的寡糖在医疗，制药和农业应用领域中可能被证明是重要的。此外，观察到（1,3）-β-D-葡聚糖葡糖合酶在其受体亚位点中容纳了（1,3）-，（1,4），-和（1,6）-β-寡糖，但来自高等植物的野生型（1,3）-β-D-葡聚糖内切酶的生理作用却出乎意料。

  DOI：

  10.1002/chem.200304733