(3-hydroxy)propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 98925-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3-hydroxy)propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3-hydroxypropylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 98925-98-5
• 化学式: C₁₇H₂₆O₁₀S
• 分子量: 422.453
• InChiKey: WAJDORPBXCBTRW-UUAJXVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3-hydroxy)propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 HOF* CH₃CN 作用下， 以 氯仿 为溶剂， 反应 0.03h， 以68%的产率得到3'-hydroxypropyl 2,3,4,6-tetra-O-acetyl-1-sulfonyl-β-D-glucopyranoside
  参考文献：
  名称：

  Application of HOF·CH3CN to the synthesis of glycosyl sulfones

  摘要：

  A fast, complete and clean conversion of thioglycosides into glycosyl sull'ones under mild acidic conditions is described, using the HOF center dot CH3CN complex at room temperature. This methodology affords glycosyl sull'ones in high yields and in excellent purity. (c) 2008 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2008.05.033
• 作为产物：
  描述：

  2-(2,3,4,6-四邻乙酰基-beta-d-吡喃葡萄糖)-2-硫代异脲氢溴酸 在 sodium metabisulfite 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 5.0h， 生成 (3-hydroxy)propyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] PHOTODYNAMIC THERAPY AND DIAGNOSIS
  [FR] THÉRAPIE ET DIAGNOSTIC PHOTODYNAMIQUES

  摘要：

  The present invention relates to phyllochlorin analogues and their pharmaceutically acceptable salts, and compositions comprising phyllochlorin analogues and their pharmaceutically acceptable salts. Phyllochlorin analogues and pharmaceutically acceptable salts thereof are suitable for use in photodynamic therapy, cytoluminescent therapy and photodynamic diagnosis, for example, for treating or detecting a tumour, or for antiviral treatment. The present invention also relates to the use of phyllochlorin analogues and pharmaceutically acceptable salts thereof in the manufacture of a phototherapeutic or photodiagnostic agent, and to a method of photodynamic therapy, cytoluminescent therapy or photodynamic diagnosis, for example, for treating or detecting a tumour, or for antiviral treatment.

  公开号：

  WO2023094677A1

文献信息

• The glucosinolate–myrosinase system. New insights into enzyme–substrate interactions by use of simplified inhibitors
  作者：Aurélie Bourderioux、Myriam Lefoix、David Gueyrard、Arnaud Tatibouët、Sylvain Cottaz、Steffi Arzt、Wim P. Burmeister、Patrick Rollin

  DOI：10.1039/b502990b

  日期：——

  Myrosinase, a thioglucoside glucohydrolase, is the only enzyme able to hydrolyse glucosinolates, a unique family of molecules bearing an anomeric O-sulfated thiohydroximate function. Non-hydrolysable myrosinase inhibitors have been devised and studied for their biological interaction. Diverse modifications of the O-sulfate moiety did not result in a significant inhibitory effect, whereas replacing the D-glucopyrano residue by its carba-analogue allowed inhibition to take place. X-Ray experiments carried out after soaking allowed for the first time inclusion of a non-hydrolysable inhibitor inside the enzymatic pocket. Structural tuning of the aglycon part in its pocket is being used as a guide for the development of simplified and more potent inhibitors.

  甲酰基酶（Myrosinase）是一种硫糖苷葡萄糖水解酶，是唯一能水解葡萄糖异硫氰酸酯的酶。葡萄糖异硫氰酸酯是一类独特的分子，具有亚胺氧硫酸盐功能。已经设计并研究了非水解性甲酰基酶抑制剂及其生物相互作用。对O-硫酸酯部分的多样性改造未能产生显著的抑制效果，而将D-葡萄糖基残基替换为其碳烯类似物则实现了抑制。浸泡后进行的X射线实验首次实现了非水解性抑制剂在酶口袋内的包封。对其口袋中非糖部分的结构调节被用作开发简化和更有效抑制剂的指导。
• Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions
  作者：Kim Le Mai Hoang、Yaguang Bai、Xin Ge、Xue-Wei Liu

  DOI：10.1021/jo400020q

  日期：2013.6.7

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.
• Radical functionalization of thioglycosides in aqueous medium
  作者：Sarbjeet Kaur、Dominic P. Luciano、Xinhao Fan、Gaoyuan Zhao、Sheridan Messier、Madison M. Walker、Qiang Zhang、Ting Wang

  DOI：10.1016/j.tetlet.2021.153499

  日期：2021.12