(E)-5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine | 674781-08-9

• 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: (E)-5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine
• 英文别名: prop-2-enyl N-[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-(phenylmethoxycarbonylamino)oxolan-2-yl]methyl]carbamate
• CAS: 674781-08-9
• 化学式: C₂₃H₂₅BrN₄O₇
• 分子量: 549.378
• InChiKey: QCDDNTSIBYWTIN-FIIXJZFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (E)-5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine 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81%的产率得到(E)-5'-amino-3'-benzyloxycarbonylamino-5-(2-bromoallyl)-2',3',5'-trideoxyuridine
  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：

  (E)-3',5'-diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine 在 Candida antarctica lipase B 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 生成 (E)-5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine
  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.