cyclohexyl-cyclohexylcarbamoyl-phosphoramidic acid mono-((6aS)-4-amino-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-yl) ester | 55036-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: cyclohexyl-cyclohexylcarbamoyl-phosphoramidic acid mono-((6aS)-4-amino-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-yl) ester
• 英文别名: arabino-8,O^2'-cyclo-[3']adenylic acid mono-(cyclohexyl-cyclohexylcarbamoyl-amide)
• CAS: 55036-16-3
• 化学式: C₂₃H₃₄N₇O₇P
• 分子量: 551.539
• InChiKey: QWTRYCDOWJIFDE-LAVAIGHBSA-N

反应信息

• 作为产物：
  描述：

  cyclohexyl-cyclohexylcarbamoyl-phosphoramidic acid mono-[(6aS)-4-amino-8t-(4-methoxy-trityloxymethyl)-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-yl] ester 在 水 、 溶剂黄146 作用下， 生成 cyclohexyl-cyclohexylcarbamoyl-phosphoramidic acid mono-((6aS)-4-amino-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-7c-yl) ester
  参考文献：
  名称：

  Polynucleotides. XXVI. Synthesis of an AUG analog, 8,2'-anhydro-8-oxy-9-.BETA.-D-arabinofuranosyladenine phosphoryl-(3'-5')-uridylyl-(3'-5')-guanosine.

  摘要：

  A triplet AUG analog containing 8, 2'-O-cycloadenosine in the first position was synthesized. Starting from 2'-O-(2, 4, 6-triisopropylbenzenesulfonyl)-8-bromoadenosine (I), 5'-monomethoxytrityl-8, 2'-O-cycloadenosine (IV) was synthesized via 8-oxy derivative (II) by the successive treatment with sodium acetate, monomethoxytrityl chloride and methanolic ammonia. Phosphorylation of compound IV with cyanoethyl phosphate and dicyclohexylcarbodiimide (DCC) at 18-20° for 5 days gave only 3'-cyanoethylphosphate (V) quantitatively. Treatment of V with methanolic ammonia gave 3'-phosphate (VI) in a relatively low yield with concomitant formation of 2', 3'-cyclic phosphate (VII). Compound VI was then condensed with 2'-O-benzoyluridylyl-(3'-5')-N2, 2', 3'-triisobutyrylguanosine (X) using DCC and after purification on a column of diethylaminoethyl (DEAE)-cellulose, 8, 2'-O-cycloadenylyl-(3'-5')-guanosine (XI) was obtained in a yield of 4.1%. Compound XI showed hypochromicity of 7.3% at 257 nm and circular dichroism (CD) spectra taken at 0° and 20° revealed that this trinucleotide exists in a rather freely rotatable, unstacked form both at these temperatures.

  DOI：

  10.1248/cpb.22.2578