phenylthio-1-deoxy-2,3,4-tri-O-benzoyl-6-O-trutyl-β-D-galactoside | 864776-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: phenylthio-1-deoxy-2,3,4-tri-O-benzoyl-6-O-trutyl-β-D-galactoside
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-phenylsulfanyl-2-(trityloxymethyl)oxan-3-yl] benzoate
• CAS: 864776-72-7
• 化学式: C₅₂H₄₂O₈S
• 分子量: 826.967
• InChiKey: DFLMNDXLWQVUTG-BCXJKZJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  61
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenylthio-1-deoxy-2,3,4-tri-O-benzoyl-6-O-trutyl-β-D-galactoside 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations

  摘要：

  Isopropenyl glycosides (i.e., 10 and 11) have been synthesized in high yields by reacting the corresponding anomeric acetates with the Tebbe reagent. These compounds undergo glycosylation with primary or secondary carbohydrate alcohols in the presence of trimethylsilyl triflate or boron trifluoride etherate, probably via a mixed acetal glycoside intermediate. On the basis of this principle, a quite efficient glycosylation of monosaccharide hemiacetal donors (i.e., 1, 7, and 9) with acceptors bearing an isopropenyl ether function at a primary or secondary position (i.e., 18 and 21) has been developed. Also investigated were the glycosylating properties of isopropenyl glucosyl and galactosyl carbonates (i.e., 12-15), easily prepared from the corresponding hemiacetals, toward sugar alcohols. In each case, the beta-selective synthesis of disaccharides from donors having nonparticipating groups at C-2 was ensured by the use of acetonitrile, at low temperature, as the solvent.

  DOI：

  10.1021/ja00042a010
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 42.0h， 生成 phenylthio-1-deoxy-2,3,4-tri-O-benzoyl-6-O-trutyl-β-D-galactoside
  参考文献：
  名称：

  唾液酸化聚糖链的不同合成：聚合物载体，树脂捕获释放和化学酶策略的组合使用。

  摘要：

  DOI：

  10.1002/anie.200500777

文献信息

• Synthesis of 3,6-branched arabinogalactan-type tetra- and hexasaccharides for characterization of monoclonal antibodies
  作者：Anikó Fekete、Anikó Borbás、Sándor Antus、András Lipták

  DOI：10.1016/j.carres.2009.04.025

  日期：2009.8

  Synthesis of tetra- and hexasaccharides built up from a beta-(1 -> 6)-linked galactopyranosyl backbone with arabinofuranosyl side chains at position 3 and with a 3-aminopropyl spacer related to arabinogalactans is described. These oligosaccharides were prepared for investigation of monoclonal antibodies raised against arabinogalactan proteins (AGPs) from pressed juice of Echinacea purpurea. (C) 2009 Elsevier Ltd. All rights reserved.