5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-3',5'-dideoxythymidine | 674781-07-8

• 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: 5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-3',5'-dideoxythymidine
• 英文别名: prop-2-enyl N-[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-(phenylmethoxycarbonylamino)oxolan-2-yl]methyl]carbamate
• CAS: 674781-07-8
• 化学式: C₂₂H₂₆N₄O₇
• 分子量: 458.471
• InChiKey: RBYXTFIKGXEKQV-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-3',5'-dideoxythymidine 在 bis-triphenylphosphine-palladium(II) chloride 三正丁基氢锡 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到5'-amino-3'-benzyloxycarbonylamino-3',5'-dideoxythymidine
  参考文献：
  名称：

  First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues

  摘要：

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.

  DOI：

  10.1021/jo035678m
• 作为产物：
  描述：

  3',5'-Diamino-3',5'-dideoxythymidine 在 Candida antarctica lipase B 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-3',5'-dideoxythymidine
  参考文献：
  名称：

  First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues

  摘要：

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.

  DOI：

  10.1021/jo035678m

文献信息

• First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues
  作者：Iván Lavandera、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/jo035678m

  日期：2004.3.1

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.