2,3-di-O-tert-butyldimethylsilyl-D-glucono-1,4-lactone | 200809-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,3-di-O-tert-butyldimethylsilyl-D-glucono-1,4-lactone
• 英文别名: (3R,4S,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(1R)-1,2-dihydroxyethyl]oxolan-2-one
• CAS: 200809-91-2
• 化学式: C₁₈H₃₈O₆Si₂
• 分子量: 406.667
• InChiKey: PPGLNXQFFLACKW-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-di-O-tert-butyldimethylsilyl-D-glucono-1,4-lactone 在 吡啶 、 咪唑 、 甲醇 、 sodium azide 、 氧化汞红 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.92h， 生成 (3R,4S,5S)-5-[(R)-1-Azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one
  参考文献：
  名称：

  Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a d-glucotriazole carboxylate

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(97)00561-2
• 作为产物：
  描述：

  在 咪唑 、 盐酸 、 20 % Pd(OH)2/C 、 水 、 氢气 、 silver carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.0h， 生成 2,3-di-O-tert-butyldimethylsilyl-D-glucono-1,4-lactone
  参考文献：
  名称：

  First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata

  摘要：

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.105

文献信息

• 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。
• First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata
  作者：Masaki Takahashi、Yusuke Murata、Yuki Hakamata、Kohei Suzuki、Tetsuya Sengoku、Hidemi Yoda

  DOI：10.1016/j.tet.2012.06.105

  日期：2012.9

  The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from D-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.