2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone | 196494-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone
• 英文别名: 2,3-bis-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-D-glucono-1,4-lactone；(3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 196494-81-2
• 化学式: C₂₁H₄₂O₆Si₂
• 分子量: 446.732
• InChiKey: WLEGOSFUHSRCDC-WCXIOVBPSA-N

物化性质

• 沸点：
  449.4±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone 在 吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 三氯化硼 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.08h， 生成 L-木糖
  参考文献：
  名称：

  由d-葡萄糖酸内酯合成l-果糖和l-木糖

  摘要：

  从d-葡萄糖醛酸1,5-内酯以47％的产率合成了l-古洛糖，其是博来霉素A 2的抗生素和抗肿瘤活性的必需成分。在叔丁基二甲基甲硅烷基醚存在下，SnCl 2对丙酮化物的有效裂解是重要的。精心设计的d-葡萄糖基1,5-内酯，包括由Dess-Martin高碘烷氧化降解的步骤，也获得了可观的L-木糖收率。

  DOI：

  10.1016/s0040-4020(01)01146-2
• 作为产物：
  描述：

  5,6-O-isopropylidene-D-glucono-1,4-lactone 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-glucono-1,4-lactone
  参考文献：
  名称：

  Inhibition of UDP-Gal Mutase and Mycobacterial Galactan Biosynthesis by Pyrrolidine Analogues of Galactofuranose

  摘要：

  Some pyrrolidine analogues of galactofuranose - synthesised from carbohydrate lactones - are the first known inhibitors of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis.:This inhibition may form a new chemotherapeutic strategy for the treatment of human pathogens which contain integral galactofuranosyl structures such as tuberculosis and leprosy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01539-6

文献信息

• Expeditious synthesis of C-glycosyl conjugated dienes and aldehydes from sugar lactones
  作者：Wen-Bin Yang、Chuan-Fa Chang、Shwu-Huey Wang、Chin-Fen Teo、Chun-Hung Lin

  DOI：10.1016/s0040-4039(01)00814-0

  日期：2001.7

  Several C-glycosyl conjugated dienes were prepared in two steps from protected sugar lactones via addition of allylmagnesium chloride and the subsequent dehydration. A sequence of allylic addition, ozonolysis and dehydration led to the corresponding glycosyl conjugated aldehydes. These conjugated functionalities can be used as diagnostic chromophores for sugar synthesis and purification. The synthetic

  通过添加烯丙基氯化镁并随后进行脱水，由受保护的糖内酯分两步制备几种C-糖基共轭二烯。一系列烯丙基加成，臭氧分解和脱水导致相应的糖基缀合的醛。这些共轭的功能可以用作糖合成和纯化的诊断生色团。还进行了糖基二烯的合成研究。糖二烯的氢硼化取决于后处理条件而导致均一醇或螺缩醛。
• The expeditious preparation and reactivity of some protected forms of gluconolactones
  作者：Wen-Bin Yang、Cheng-Hsin Tsai、Chun-Hung Lin

  DOI：10.1016/s0040-4039(00)00207-0

  日期：2000.4

  2,3-Bis-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-d-glucono-1,4-lactone has been easily prepared from commercially available starting material and its activity investigated. Based on the lactone functionality, this compound can proceed via nucleophilic addition, reduction, and hydrolysis to generate various highly functionalized molecules.

  2,3-双-O-（叔丁基二甲基甲硅烷基）-5,6 - O-异亚丙基-d-葡萄糖基-1,4-内酯很容易从商购的起始原料中制备，并对其活性进行了研究。基于内酯官能度，该化合物可通过亲核加成，还原和水解进行反应，以生成各种高度官能化的分子。
• Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate
  作者：Thomas M. Krülle、Carmen de la Fuente、Lea Pickering、Robin T. Aplin、Katerina E. Tsitsanou、Spyros E. Zographos、Nikos G. Oikonomakos、Robert J. Nash、Rhodri C. Griffiths、George W.J. Fleet

  DOI：10.1016/s0957-4166(97)00561-2

  日期：1997.11

  Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.
• The synthesis of l-gulose and l-xylose from d-gluconolactone
  作者：Wen-Bin Yang、Sachindra S Patil、Cheng-Hsin Tsai、Chun-Hung Lin、Jim-Min Fang

  DOI：10.1016/s0040-4020(01)01146-2

  日期：2002.1

  ethers was of importance in the course of synthesis. Elaboration of d-glucono-1,5-lactone that includes a step of oxidative degradation by Dess–Martin periodinane also afforded a respectable yield of l-xylose.

  从d-葡萄糖醛酸1,5-内酯以47％的产率合成了l-古洛糖，其是博来霉素A 2的抗生素和抗肿瘤活性的必需成分。在叔丁基二甲基甲硅烷基醚存在下，SnCl 2对丙酮化物的有效裂解是重要的。精心设计的d-葡萄糖基1,5-内酯，包括由Dess-Martin高碘烷氧化降解的步骤，也获得了可观的L-木糖收率。
• Inhibition of UDP-Gal Mutase and Mycobacterial Galactan Biosynthesis by Pyrrolidine Analogues of Galactofuranose
  作者：Richard E Lee、Martin D. Smith、Robert J. Nash、Rhodri C. Griffiths、Michael McNeil、Ravinder K. Grewal、Wenxin Yan、Gurdyal S. Besra、Patrick J. Brennan、George W.J. Fleet

  DOI：10.1016/s0040-4039(97)01539-6

  日期：1997.9

  Some pyrrolidine analogues of galactofuranose - synthesised from carbohydrate lactones - are the first known inhibitors of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis.:This inhibition may form a new chemotherapeutic strategy for the treatment of human pathogens which contain integral galactofuranosyl structures such as tuberculosis and leprosy. (C) 1997 Elsevier Science Ltd.