S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside | 403646-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside
• 英文别名: (3aR,4S,6S,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-6-methyl-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 403646-44-6
• 化学式: C₁₉H₂₈O₅SSi
• 分子量: 396.58
• InChiKey: ZXLKSXKAYBWYBV-RDDKANTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-carbonyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides

  摘要：

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

  DOI：

  10.1021/jo0108818
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 S-phenyl 2,3-O-carbonyl-1-thio-α-L-rhamnopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides

  摘要：

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

  DOI：

  10.1021/jo0108818

文献信息

• Synthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides
  作者：David Crich、Hongmei Li

  DOI：10.1021/jo0108818

  日期：2002.7.1

  A synthesis of a chromogenic glycoside of the Salmonella anatum group E-1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyI thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.