acetic acid 6-(tert-butyldimethylsilanoxymethyl)-2,2-dimethyl-4-(3-cyanothiophen-5-yl)-tetrahydrofuro[3,4-a][1,3]dioxol-4-yl ester | 763139-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid 6-(tert-butyldimethylsilanoxymethyl)-2,2-dimethyl-4-(3-cyanothiophen-5-yl)-tetrahydrofuro[3,4-a][1,3]dioxol-4-yl ester
• 英文别名: 1-O-acetyl-5-O-tert-butyldimethylsilyl-2,3-O,O-isopropylidene-1-(5-thiophene-2-carbonitrile)-α-D-ribofuranose
• CAS: 763139-78-2
• 化学式: C₂₁H₃₁NO₆SSi
• 分子量: 453.632
• InChiKey: JQWJNSLEDAQGOD-FLTJSSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  87.01
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  acetic acid 6-(tert-butyldimethylsilanoxymethyl)-2,2-dimethyl-4-(3-cyanothiophen-5-yl)-tetrahydrofuro[3,4-a][1,3]dioxol-4-yl ester 在 三乙基硅烷 、 磷酸三乙酯 、 三氟甲磺酸三甲基硅酯 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 phosphoric acid mono-[5(R)-(2-cyanothiophen-5-yl)-3,4-dihydroxytetrahydrofuran-2-yl-methyl] ester
  参考文献：
  名称：

  Novel nicotinamide adenine dinucleotide analogues as selective inhibitors of NAD+-dependent enzymes

  摘要：

  Three novel dinucleotide analogues of nicotinamide adenine dinucleotide (NAD(+)) have been synthesised from D-ribonolactone. These compounds incorporate a thiophene moiety in place of nicotinamide and are hydrolytically stable. They have been evaluated as inhibitors of adenosine diphosphate ribosyl cyclase, glutamate dehydrogenase and Sir2 acyltransferase activities. Enzyme specificity and a high level of inhibition was observed for the dehydrogenase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.091
• 作为产物：
  描述：

  卡培他滨杂质25 在 4-二甲氨基吡啶 、 potassium permanganate 、 正丁基锂 、 HCR-W₂ H⁺-Dowex resin 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 正戊烷 为溶剂， 反应 13.0h， 生成 acetic acid 6-(tert-butyldimethylsilanoxymethyl)-2,2-dimethyl-4-(3-cyanothiophen-5-yl)-tetrahydrofuro[3,4-a][1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Novel nicotinamide adenine dinucleotide analogues as selective inhibitors of NAD+-dependent enzymes

  摘要：

  Three novel dinucleotide analogues of nicotinamide adenine dinucleotide (NAD(+)) have been synthesised from D-ribonolactone. These compounds incorporate a thiophene moiety in place of nicotinamide and are hydrolytically stable. They have been evaluated as inhibitors of adenosine diphosphate ribosyl cyclase, glutamate dehydrogenase and Sir2 acyltransferase activities. Enzyme specificity and a high level of inhibition was observed for the dehydrogenase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.091