(1S,3R,4R,5R,6S,7S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester | 175273-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,5R,6S,7S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester
• CAS: 175273-79-7
• 化学式: C₂₈H₅₈O₆Si₃
• 分子量: 575.021
• InChiKey: UAGWUXIYJNHIDY-ZIKOEFHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R,6S,7S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester 在 盐酸 、 sodium cyanide 、 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 104.0h， 生成 ethyl 2-C-carbamoylmethyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†

  摘要：

  Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining a-glucosidase from barley.

  DOI：

  10.1081/car-200067125
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 咪唑 、 dirhodium tetraacetate 、 N,N'-bis(salicylidene)ethylenediaminatooxovanadium(IV) 、 ammonium chloride 、 氢溴酸 、 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,3R,4R,5R,6S,7S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxa-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases†

  摘要：

  Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining a-glucosidase from barley.

  DOI：

  10.1081/car-200067125

文献信息

• Cyclopropanation of unsaturated sugars with ethyl Diazoacetate
  作者：John O. Hoberg、David J. Claffey

  DOI：10.1016/0040-4039(96)00335-8

  日期：1996.4

  The cyclopropanation of unsaturated sugars with ethyl diazoacetate and a metal catalyst provides ester-substituted 1,2-C-methylene carbohydrates in good to excellent yields. Ring opening of the cyclopropane has also been achieved providing C-2 branched glycosyl bromides.

  用重氮乙酸乙酯和金属催化剂对不饱和糖进行环丙烷化，可以很好地获得优良的酯取代的1,2- C-亚甲基碳水化合物。提供C-2支链的糖基溴化物也可以实现环丙烷的开环。
• Simple Synthesis of 1,2‐Dideoxy‐2‐Vinyl Carbohydrates by Tin‐Free Radical Reactions of Xanthates
  作者：Yasemin Mai‐Linde、Torsten Linker

  DOI：10.1002/chem.202302118

  日期：2024.1.2

  Radical and non-toxic: C-Branched carbohydrates 3 are easily available from glycals 1 via xanthates 2. Key step is a radical reaction with triethylborane, which proceeds under mild conditions with high regioselectivity. Various side products have been isolated in pure form. They speak for a reversible ring-opening of the intermediary cyclopropylmethyl radicals, which is interesting for the mechanistic

  自由基且无毒： C支链碳水化合物3很容易从糖醛1经由黄原酸盐2获得。关键步骤是与三乙基硼烷发生自由基反应，该反应在温和条件下进行，具有高区域选择性。各种副产物已以纯品形式分离出来。它们代表中间环丙基甲基自由基的可逆开环，这对于理解此类反应的机理很有趣。
• Rhodium(II) catalyzed asymmetric cyclopropanation of glycals with ethyl diazoacetate
  作者：Cornelis M. Timmers、Michiel A. Leeuwenburgh、Jeroen C. Verheijen、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0957-4166(95)00418-1

  日期：1996.1

  Carbenoid species generated from ethyl diazoacetate and catalytic Rh-2(OAc)(4) react smoothly and with a high degree of stereoselectivity with glycals resulting in the predominant formation of doubly branched adducts containing an alpha-exo-orientated ethyl cyclopropanecarboxylate moiety.