Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester | 314297-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
• 英文别名: [(3aR,5S,6S,6aR)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-6-[(4-methylphenyl)sulfonylamino]-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 314297-16-0
• 化学式: C₃₉H₄₇NO₉S₂Si
• 分子量: 766.021
• InChiKey: GARKHHDJJGLNKU-QXIHPRNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 在 4-二甲氨基吡啶 、 戊醇 、 三氟甲磺酸三甲基硅酯 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 硫酸 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 生成 Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6
• 作为产物：
  描述：

  3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6

文献信息

• Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer
  作者：Satoshi Obika、Jyun-ichi Andoh、Mayumi Onoda、Osamu Nakagawa、Akiko Hiroto、Tomomi Sugimoto、Takeshi Imanishi

  DOI：10.1016/s0040-4039(03)01279-6

  日期：2003.7

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.