3-deoxy-3-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-ribofuranose | 19029-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]ethanol
• CAS: 19029-59-5
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: IQLNXZAAEDRRLD-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-ribofuranose 在 吡啶 、 溴 、 potassium carbonate 、 barium benzoate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 methyl (2R,3R,4S)-3-(2-phenylmethoxyethyl)-4-(phenylmethoxymethyl)oxetane-2-carboxylate
  参考文献：
  名称：

  Ring contraction of 3-deoxy-2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)97209-5
• 作为产物：
  描述：

  5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 在 sodium tetrahydroborate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-deoxy-3-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹

  摘要：

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.

  DOI：

  10.1021/jo991399g

文献信息

• A simple one-pot entry to cyclic ethers of varied ring sizes from diols via phosphonium ion induced iodination and base catalyzed Williamson etherification
  作者：Biswajit Gopal Roy、Ashim Roy、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2006.08.090

  日期：2006.10

  A novel and an efficient one-pot cyclization method using triphenylphosphine, iodine and a nitrogenous base has been established for the synthesis of cyclic ethers of various ring sizes. This appears to follow a two-step procedure, which includes preferential substitution of one hydroxyl group by an iodide generated in situ followed by an intramolecular ring closure through the attack of a free hydroxyl

  已经建立了使用三苯基膦，碘和含氮碱的新颖且有效的一锅环化方法，用于合成各种环大小的环醚。这似乎遵循两步程序，其中包括一个羟基被原位生成的碘优先取代，然后通过游离羟基或更多亲核性氧化物离子的攻击而分子内闭环。
• WITTY, D. R.;FLEET, G. W. J.;CHOI, S.;VOGT, K.;WILSON, E. X.;WANG, Y.;STO+, TETRAHEDRON LETT., 31,(1990) N7, C. 6927-6930
  作者：WITTY, D. R.、FLEET, G. W. J.、CHOI, S.、VOGT, K.、WILSON, E. X.、WANG, Y.、STO+

  DOI：——

  日期：——
• Ring contraction of 3-deoxy-2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetanes
  作者：D.R. Witty、G.W.J. Fleet、S. Choi、K. Vogt、F.X. Wilson、Y. Wang、R. Storer、P.L. Myers、C.J. Wallis

  DOI：10.1016/s0040-4039(00)97209-5

  日期：1990.1
• Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹
  作者：Morris J. Robins、Bogdan Doboszewski、Victor A. Timoshchuk、Matt A. Peterson

  DOI：10.1021/jo991399g

  日期：2000.5.1

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.