6-amino-9-[(3S,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-yl]purine | 690661-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-amino-9-[(3S,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-yl]purine
• 英文别名: 9-[(3R,4R,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl]purin-6-amine
• CAS: 690661-05-3
• 化学式: C₂₄H₂₅N₅O₃
• 分子量: 431.494
• InChiKey: OLBRPAMBGNZOFG-KCZVDYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-9-[(3S,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-yl]purine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 6-amino-9-[(3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]purine
  参考文献：
  名称：

  Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside

  摘要：

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.121
• 作为产物：
  描述：

  1,4-anhydro-3,5-di-O-benzyl-D-xylitol 在 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 66.0h， 生成 6-amino-9-[(3S,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-yl]purine
  参考文献：
  名称：

  Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside

  摘要：

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.121

文献信息

• Simple entry into isonucleosides: synthesis of 6-amino-9-[(3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]purine
  作者：Hari Babu Mereyala、Sreeman Kumar Mamidyala

  DOI：10.1016/j.tetlet.2004.02.021

  日期：2004.3

  A simple and efficient method for the preparation of isonucleoside 7 is described. The preparation of 1,4-anhydroxylitol 4, a key intermediate, is described by intramolecular cyclization of (2S,3R,4R)-3,5-dibenzyloxypentan-1,2,4-triol 3 using diethyl carbonate and NaH. (C) 2004 Published by Elsevier Ltd.
• Deoxygenation/dimerization of sugar derivatives with BF3·Et2O–Et3SiH: synthesis of a β-isonucleoside
  作者：Subhrangshu Mukherjee、Biswajit G. Roy、Soumendra N. Das、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2012.06.121

  日期：2012.9

  Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained as the sole products, while only the dimeric products are isolated if Et3SiH is excluded. One of the deoxygenated products has been transformed into a beta-isonucleoside. (C) 2012 Elsevier Ltd. All rights reserved.