2-(2,3-O-Isopropylidene-5-O-trityl-β-D-ribofuranosyl)acetonitrile | 56703-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(2,3-O-Isopropylidene-5-O-trityl-β-D-ribofuranosyl)acetonitrile
• 英文别名: 2-[(3aR,4R,6S,6aS)-2,2-dimethyl-4-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]acetonitrile
• CAS: 56703-40-3
• 化学式: C₂₉H₂₉NO₄
• 分子量: 455.554
• InChiKey: GWNPSTSZTQOLFT-YYGZZXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,3-O-Isopropylidene-5-O-trityl-β-D-ribofuranosyl)acetonitrile 在 盐酸 、 氨 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 巯基乙酸乙酯 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 80.0h， 生成 3-α-D-Ribofuranosylisothiazolo<4,5-d>pyrimidin-7(6H)-one hydrochloride
  参考文献：
  名称：

  Efficient synthesis of fused isothiazole C-nucleosides. 1. Synthesis of a 3-.beta.-D-ribofuranosylisothiazolo[4,5-d]pyrimidin-7(6H)-one isostere of inosine

  摘要：

  The reaction of 2-(2,3-O-isopropylidene-5-O-trityl-beta-D-ribofuranosyl)acetonitrile (6) with isopentyl nitrite/NaH and subsequent tosylation of Na-oximino nitrile 7 gave protected 2-D-ribofuranosyl-2-(tosyloximino)acetonitriles 9alpha,beta as novel C-nucleoside precursors. Treatment of 9alpha,beta with ethyl 2-mercaptoacetate under basic conditions afforded epimeric ethyl 4-aminoisothiazole-5-carboxylate C-nucleosides 10alpha,beta. Cyclization of 10alpha,beta to the desired 3-D-ribofuranosylisothiazolo[4,5-d]pyrimidin-7(6H)-ones 14alpha,beta was accomplished by the reaction of 10alpha,beta with triethyl orthoformate and subsequent amminolysis. Deprotection of 14beta and 14alpha in 7% HCl/MeOH gave the title compound 3 and alpha-isomeric C-nucleoside 4 as monohydrochloride salt, respectively. The configuration of C-glycoside 9alpha was established by X-ray crystallography.

  DOI：

  10.1021/jo00071a030
• 作为产物：
  描述：

  2,3-O-isopropylidene-β-D-ribofuranose 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 18.0h， 生成 2-(2,3-O-Isopropylidene-5-O-trityl-β-D-ribofuranosyl)acetonitrile
  参考文献：
  名称：

  [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS
  [FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING

  摘要：

  公开号：

  WO2018138685A3

文献信息

• US4096321A
  申请人：——

  公开号：US4096321A

  公开（公告）日：1978-06-20
• US4161582A
  申请人：——

  公开号：US4161582A

  公开（公告）日：1979-07-17
• [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS<br/>[FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING
  申请人：JANSSEN BIOTECH INC

  公开号：WO2018138685A3

  公开（公告）日：2018-10-04
• Efficient synthesis of fused isothiazole C-nucleosides. 1. Synthesis of a 3-.beta.-D-ribofuranosylisothiazolo[4,5-d]pyrimidin-7(6H)-one isostere of inosine
  作者：Heinrich Wamhoff、Rainer Berressem、Martin Nieger

  DOI：10.1021/jo00071a030

  日期：1993.9

  The reaction of 2-(2,3-O-isopropylidene-5-O-trityl-beta-D-ribofuranosyl)acetonitrile (6) with isopentyl nitrite/NaH and subsequent tosylation of Na-oximino nitrile 7 gave protected 2-D-ribofuranosyl-2-(tosyloximino)acetonitriles 9alpha,beta as novel C-nucleoside precursors. Treatment of 9alpha,beta with ethyl 2-mercaptoacetate under basic conditions afforded epimeric ethyl 4-aminoisothiazole-5-carboxylate C-nucleosides 10alpha,beta. Cyclization of 10alpha,beta to the desired 3-D-ribofuranosylisothiazolo[4,5-d]pyrimidin-7(6H)-ones 14alpha,beta was accomplished by the reaction of 10alpha,beta with triethyl orthoformate and subsequent amminolysis. Deprotection of 14beta and 14alpha in 7% HCl/MeOH gave the title compound 3 and alpha-isomeric C-nucleoside 4 as monohydrochloride salt, respectively. The configuration of C-glycoside 9alpha was established by X-ray crystallography.