Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4,6-dihydroxy-4,6-dioxo-2-thioxo-2λ⁵,4λ⁵,6λ⁵-[1,3,5,2,4,6]trioxatriphosphinan-2-yloxymethyl)-5-(2-imino-6-oxo-1,2,3,6-tetrahydro-purin-9-yl)-tetrahydro-furan-3-yl ester | 118275-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4,6-dihydroxy-4,6-dioxo-2-thioxo-2λ⁵,4λ⁵,6λ⁵-[1,3,5,2,4,6]trioxatriphosphinan-2-yloxymethyl)-5-(2-imino-6-oxo-1,2,3,6-tetrahydro-purin-9-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-4-acetyloxy-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[(4,6-dihydroxy-4,6-dioxo-2-sulfanylidene-1,3,5,2lambda5,4lambda5,6lambda5-trioxatriphosphinan-2-yl)oxymethyl]oxolan-3-yl] acetate；[(2R,3R,4R,5R)-4-acetyloxy-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[(4,6-dihydroxy-4,6-dioxo-2-sulfanylidene-1,3,5,2λ5,4λ5,6λ5-trioxatriphosphinan-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 118275-94-8
• 化学式: C₁₄H₁₈N₅O₁₄P₃S
• 分子量: 605.309
• InChiKey: LTYAHEWTFBNIAX-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  291
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4,6-dihydroxy-4,6-dioxo-2-thioxo-2λ⁵,4λ⁵,6λ⁵-[1,3,5,2,4,6]trioxatriphosphinan-2-yloxymethyl)-5-(2-imino-6-oxo-1,2,3,6-tetrahydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 ammonium hydroxide 、 lithium sulfide 作用下， 生成 guanosine 5'-O-(1,1-dithiotriphosphate)
  参考文献：
  名称：

  Synthesis of nucleoside 5'-O-(1,3-dithiotriphosphates) and 5'-O-(1,1-dithiotriphosphates)

  摘要：

  The synthesis of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) as the first example of a nucleoside 5'-O-(1,3-dithiotriphosphate) is described. 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one phosphitylates the 5'-hydroxy group of 3'deoxy-3'-azidothymidine to form intermediate 1. Reaction of 1 with thiopyrophosphate (9) and sulfur results in the formation of an unseparable mixture of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) and 3'-deoxy-3'-azidothymidine 5'-O-(1,2-dithiotriphosphate) (3). Selective hydrolysis of 5 allows isolation of 3. However, reaction of 1 with P1-O-(cyanoethyl)-P1-thiopyrophosphate (8) and sulfur produced the diastereomers of 5 in good yield. Compound 8 is prepared by reaction of 3-hydroxyproprionitrile with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one, pyrophosphate, and sulfur to yield 10, which is ring opened to 8 by reaction with ethylenediamine. Hydrolysis of this compound leads to 9. An alternative route to nucleoside 5'-O-(1,3-dithiotriphosphates) consists of reacting a nucleoside 5'-O-(1-thiocyclotriphosphate) such as 13 with Li2S. This reaction, when performed in pyridine/dioxane, leads to a mixture of the nucleoside 5'-O-(1,3-dithiotriphosphate) and the nucleoside 5'-O-(1,1-dithiotriphosphate). The latter is the only nucleotide product when the reaction is carried out in DMF.

  DOI：

  10.1021/jo00005a023
• 作为产物：
  描述：

  2',3'-di-O-acetylguanosine 在 吡啶 、 三正丁胺 、 三丁基焦磷酸铵 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4,6-dihydroxy-4,6-dioxo-2-thioxo-2λ⁵,4λ⁵,6λ⁵-[1,3,5,2,4,6]trioxatriphosphinan-2-yloxymethyl)-5-(2-imino-6-oxo-1,2,3,6-tetrahydro-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of nucleoside 5'-O-(1,3-dithiotriphosphates) and 5'-O-(1,1-dithiotriphosphates)

  摘要：

  The synthesis of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) as the first example of a nucleoside 5'-O-(1,3-dithiotriphosphate) is described. 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one phosphitylates the 5'-hydroxy group of 3'deoxy-3'-azidothymidine to form intermediate 1. Reaction of 1 with thiopyrophosphate (9) and sulfur results in the formation of an unseparable mixture of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) and 3'-deoxy-3'-azidothymidine 5'-O-(1,2-dithiotriphosphate) (3). Selective hydrolysis of 5 allows isolation of 3. However, reaction of 1 with P1-O-(cyanoethyl)-P1-thiopyrophosphate (8) and sulfur produced the diastereomers of 5 in good yield. Compound 8 is prepared by reaction of 3-hydroxyproprionitrile with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one, pyrophosphate, and sulfur to yield 10, which is ring opened to 8 by reaction with ethylenediamine. Hydrolysis of this compound leads to 9. An alternative route to nucleoside 5'-O-(1,3-dithiotriphosphates) consists of reacting a nucleoside 5'-O-(1-thiocyclotriphosphate) such as 13 with Li2S. This reaction, when performed in pyridine/dioxane, leads to a mixture of the nucleoside 5'-O-(1,3-dithiotriphosphate) and the nucleoside 5'-O-(1,1-dithiotriphosphate). The latter is the only nucleotide product when the reaction is carried out in DMF.

  DOI：

  10.1021/jo00005a023

文献信息

• LUDWIG, JANOS;ECKSTEIN, FRITZ, J. ORG. CHEM., 54,(1989) N, C. 631-635
  作者：LUDWIG, JANOS、ECKSTEIN, FRITZ

  DOI：——

  日期：——