[(3aR,5S,6R,6aR)-6-Cyano-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester | 330196-66-2

• 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: [(3aR,5S,6R,6aR)-6-Cyano-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3aR,5S,6R,6aR)-6-cyano-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]carbamate
• CAS: 330196-66-2
• 化学式: C₂₁H₂₆N₂O₇
• 分子量: 418.447
• InChiKey: HYYIFURXTXXLCL-OVNJDOEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,5S,6R,6aR)-6-Cyano-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以20%的产率得到1,2:5,6-di-O-isopropylidenespiro[3-deoxy-α-D-ribohexofuranose-3,5'-imidazolidine]-2',4'-dione
  参考文献：
  名称：

  Novel spirohydantoins of d-allose and d-ribose derived from glyco-α-aminonitriles

  摘要：

  The synthesis of 3-spirohydantoin derivatives of D-allose and D-ribose is reported. The key step is the stereoselective conversion of glyco-alpha -aminonitriles from ulose derivatives of D-glucose and D-xylose using titanium(IV) isopropoxide as a mild and efficient catalyst. Cyclisation of the glyco-alpha -aminonitriles give the target spirohydantoins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02294-2
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 titanium(IV) isopropylate 、 氨 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 [(3aR,5S,6R,6aR)-6-Cyano-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Novel spirohydantoins of d-allose and d-ribose derived from glyco-α-aminonitriles

  摘要：

  The synthesis of 3-spirohydantoin derivatives of D-allose and D-ribose is reported. The key step is the stereoselective conversion of glyco-alpha -aminonitriles from ulose derivatives of D-glucose and D-xylose using titanium(IV) isopropoxide as a mild and efficient catalyst. Cyclisation of the glyco-alpha -aminonitriles give the target spirohydantoins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02294-2

文献信息

• Novel spirohydantoins of d-allose and d-ribose derived from glyco-α-aminonitriles
  作者：Denis Postel、Albert Nguyen Van Nhien、Pierre Villa、Gino Ronco

  DOI：10.1016/s0040-4039(00)02294-2

  日期：2001.2

  The synthesis of 3-spirohydantoin derivatives of D-allose and D-ribose is reported. The key step is the stereoselective conversion of glyco-alpha -aminonitriles from ulose derivatives of D-glucose and D-xylose using titanium(IV) isopropoxide as a mild and efficient catalyst. Cyclisation of the glyco-alpha -aminonitriles give the target spirohydantoins. (C) 2001 Elsevier Science Ltd. All rights reserved.