(2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran | 373646-99-2

• 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: (2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran
• 英文别名: [(2R,3R,4R)-4-amino-3-phenylmethoxyoxolan-2-yl]methyl benzoate
• CAS: 373646-99-2
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: WUOCCELOTOFHJG-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 42.5h， 生成 1-[(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]uracil
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step

  摘要：

  We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (-)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (-)-19 and (+)-19, and isonucleosides (-)-22, (+)-22 and 25, from 2,3-O-isopropylidene-D-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00283-x
• 作为产物：
  描述：

  (3S,4R,5R)-5-[(benzoyloxy)methyl]-4-(benzyloxy)tetrahydrofuran-3-ol 在 吡啶 、 sodium azide 、 15-冠醚-5 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 75.5h， 生成 (2R,3R,4R)-4-amino-2-[(benzoyloxy)methyl]-3-(benzyloxy)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step

  摘要：

  We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (-)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (-)-19 and (+)-19, and isonucleosides (-)-22, (+)-22 and 25, from 2,3-O-isopropylidene-D-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00283-x

文献信息

• Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step
  作者：Fernando Bravo、Yolanda Dı́az、Sergio Castillón

  DOI：10.1016/s0957-4166(01)00283-x

  日期：2001.7

  We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (-)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (-)-19 and (+)-19, and isonucleosides (-)-22, (+)-22 and 25, from 2,3-O-isopropylidene-D-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved.