3-呋喃核糖基-6,7-二氢-9H-噻唑并(3,2-a)嘌呤-9-酮 | 52538-20-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 3-呋喃核糖基-6,7-二氢-9H-噻唑并(3,2-a)嘌呤-9-酮
• 中文别名: 乙酰基AF-64
• 英文名称: 3-(β-D-ribofuranosyl)-6,7-dihydrothiazolo<3,2-a>purin-9-one
• 英文别名: 3-β-D-ribofuranosyl-6,7-dihydro-3H-thiazolo[3,2-a]purin-9-one；1,S-ethane-1,2-diyl-2-thio-xanthosine；3-Ribofuranosyl-6,7-dihydro-9H-thiazolo(3,2-a)purin-9-one；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7-dihydro-[1,3]thiazolo[3,2-a]purin-9-one
• CAS: 52538-20-2
• 化学式: C₁₂H₁₄N₄O₅S
• 分子量: 326.333
• InChiKey: FHDYGGODWWOZRQ-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  阿卡地新	AICA riboside	2627-69-2	C9H14N4O5	258.234

反应信息

• 作为产物：
  描述：

  阿卡地新 、 异硫氰酸氯代乙酯 以 吡啶 为溶剂， 反应 72.0h， 以22%的产率得到3-呋喃核糖基-6,7-二氢-9H-噻唑并(3,2-a)嘌呤-9-酮
  参考文献：
  名称：

  Nucleosides. 3. Reactions of AICA-riboside with isothiocyanates. A convenient synthesis of isoguanosine and xanthosine derivatives

  摘要：

  Cyclodesulfurative annulations of 5-[1-(3-substituted-thioureido)]-1-(beta-D-ribofuranosyl)imidazole-4-carboxamides (3a-h) with N,N'-dicyclohexylacarbodiimide are described. Isoguanosine (4) and several 1-substituted isoguanosines 6a-f,h are readily prepared by a ring closure of the appropriate resulting 5-(3-substituted-1-ureido)-1-(beta-D-ribofuranosyl)imididazole-4-carbonitriles 5a-h. Treatment of the appropriate 1-substituted isoguanosines under basic conditions has furnished the corresponding 1-substituted xanthosine 12.

  DOI：

  10.1021/jo00013a026

文献信息

• CHERN, JI-WANG;LIN, GWO-SEN;CHEN, CHIEN-SHU;TOWNSEND, LEROY B., J. ORG. CHEM., 56,(1991) N3, C. 4213-4218
  作者：CHERN, JI-WANG、LIN, GWO-SEN、CHEN, CHIEN-SHU、TOWNSEND, LEROY B.

  DOI：——

  日期：——
• Nucleosides. 3. Reactions of AICA-riboside with isothiocyanates. A convenient synthesis of isoguanosine and xanthosine derivatives
  作者：Ji Wang Chern、Gwo Sen Lin、Chien Shu Chen、Leroy B. Townsend

  DOI：10.1021/jo00013a026

  日期：1991.6

  Cyclodesulfurative annulations of 5-[1-(3-substituted-thioureido)]-1-(beta-D-ribofuranosyl)imidazole-4-carboxamides (3a-h) with N,N'-dicyclohexylacarbodiimide are described. Isoguanosine (4) and several 1-substituted isoguanosines 6a-f,h are readily prepared by a ring closure of the appropriate resulting 5-(3-substituted-1-ureido)-1-(beta-D-ribofuranosyl)imididazole-4-carbonitriles 5a-h. Treatment of the appropriate 1-substituted isoguanosines under basic conditions has furnished the corresponding 1-substituted xanthosine 12.