(3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-dihydro-furan-2-one | 943129-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-dihydro-furan-2-one
• CAS: 943129-12-2
• 化学式: C₁₅H₂₈O₆Si
• 分子量: 332.469
• InChiKey: KTZISKQFVYQXHZ-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-dihydro-furan-2-one 在 2,4,5-tri-tert-butylpyrimidine 吡啶 、 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 3 A molecular sieve 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-O-benzoyl-2-O-(methyl (4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,3-di-O-benzyl-α-D-glucopyranosid)uronate)-5,6-O-isopropylidene-D-galactono-1,4-lactone
  参考文献：
  名称：

  Thioglycuronides:  Synthesis and Application in the Assembly of Acidic Oligosaccharides

  摘要：

  Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

  DOI：

  10.1021/ol049380+
• 作为产物：
  描述：

  D-半乳糖酸-1,4-内酯 在 咪唑 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (3R,4S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-dihydro-furan-2-one
  参考文献：
  名称：

  Thioglycuronides:  Synthesis and Application in the Assembly of Acidic Oligosaccharides

  摘要：

  Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

  DOI：

  10.1021/ol049380+

文献信息

• Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups
  作者：Omar Cortezano-Arellano、Camilo A. Meléndez-Becerra、Fernando Cortés、Fernando Sartillo-Piscil、Alejandro Cordero-Vargas

  DOI：10.1016/j.carres.2014.04.005

  日期：2014.7

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.