(3aS)-3c-acetoxy-2t-acetoxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine | 62840-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS)-3c-acetoxy-2t-acetoxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine
• 英文别名: O^3'_,O5'-diacetyl-arabino-2,2'-anhydro-cytidine；[(2R,4R,5R,6S)-5-acetyloxy-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-4-yl]methyl acetate
• CAS: 62840-03-3
• 化学式: C₁₃H₁₅N₃O₆
• 分子量: 309.279
• InChiKey: MHFCYSJIURNRFG-KXGXSXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aS)-3c-acetoxy-2t-acetoxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine 生成 N⁴,O^3',O^5'-Triacetyl-1-β-D-arabinofuranosylcytosine
  参考文献：
  名称：

  CHWANG, TEK L.

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 胞苷 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 生成 (3aS)-3c-acetoxy-2t-acetoxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine
  参考文献：
  名称：

  具有生物活性的核苷和核苷酸的研究。2.从嘧啶核糖核苷方便地一步合成2,2'-脱水-1-（3'，5'-二-O-酰基-β-D-阿拉伯呋喃糖基）嘧啶。

  摘要：

  DOI：

  10.1021/jo00437a003

文献信息

• Reactions of 2-acyloxyisobutyryl halides with nucleosides. 7. Synthesis and biological evaluation of some 2,2'-anhydro-1-(3',5'-di-O-acyl-.beta.-D-arabinofuranosyl)cytosine hydrochlorides
  作者：Ernest K. Hamamura、Miroslav Prystasz、Julien P. H. Verheyden、John G. Moffatt、Kenji Yamaguchi、Naomi Uchida、Kosaburo Sato、Akio Nomura、Osamu Shiratori

  DOI：10.1021/jm00227a017

  日期：1976.5

  2'-anhydro-1(beta-D-arabinofuranosyl)cytosine hydrochloride (cycloC) with a homologous series of saturated and unsaturated acyl chlorides in dimethylacetamide has been investigated. Such acylation reactions have made available a considerable number of 3',5'-diesters of cycloC that have been examined for biological activities. The compounds all show cytotoxicity against HeLa cells in tissue culture, and

  研究了2,2'-脱水-1（β-D-阿拉伯呋喃糖基）胞嘧啶盐酸盐（cycloC）在二甲基乙酰胺中与一系列饱和和不饱和酰基氯的同源性直接酰化。这样的酰化反应已经提供了相当数量的已被检测过生物学活性的cycloC 3'，5'-二酯。这些化合物都对组织培养中的HeLa细胞显示出细胞毒性，除了高度不溶的长链二酯（C16-C22）外，还对牛痘和单纯疱疹病毒显示出明显的活性。该化合物对小鼠的L1210白血病表现出不同的活性，C12-C14饱和二酯和C18-C22不饱和二酯非常有效。其他只有二亚甲基的二酯，其结果却大不相同。
• One-Step Halogenation at the 2'-Position of Uridine, and Related Reactions of Cytidine and N<SUP>4</SUP>-Acetylcytidine
  作者：RYUJI MARUMOTO、MIKIO HONJO

  DOI：10.1248/cpb.22.128

  日期：——

  The reaction of uridine with acyl bromide in acetonitrile (or ethyl acetate) afforded 3', 5'-di-O-acyl-2'-bromo-2'-deoxyuridine (II, V) in good yield, which was converted to 2'-deoxyuridine by hydrogenation and subsequent deacylation. A silmiar reaction of N4-acetylcytidine with acetyl bromide yielded 1-(2, 5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-N4-acetylcytosine (VIII), which was converted to 3'-deoxycytidine (X) by hydrogenation and subsequent deacylation with a concomitant formation of 2', 3'-dideoxycytidine (XII) and to 1-β-D-arabinofuranosyl cytosine (XI) by treatment with potassium hydroxide in ethanol. A similar reaction of cytidine with acyl bromide gave 2, 2'-anhydro-1-(3, 5-di-O-acyl-β-D-arabinofuranosyl) cytosine hydrobromide (XIV, XVI). These reaction mechanisms were also presented.

  尿苷与酰基溴在乙腈（或乙酸乙酯）中反应，可得到 3'，5'-二-O-乙酰基-2'-溴-2'-脱氧尿苷（II，V），收率很高。N4-acetylcytidine 与乙酰溴的硅烷化反应生成 1-（2，5-二-O-乙酰基-3-溴-3-脱氧-β-D-呋喃木糖基）-N4-乙酰基胞嘧啶（VIII）、在乙醇中用氢氧化钾处理后，转变为 1-β-D-arabinofuranosyl cytosine (XI)。胞苷与酰基溴发生类似反应，生成 2，2'-脱水-1-（3，5-二-O-酰基-β-D-阿拉伯呋喃糖基）胞嘧啶氢溴酸盐（XIV，XVI）。还介绍了这些反应机理。
• Studies on biologically active nucleosides and nucleotides. 2. A convenient one-step synthesis of 2,2'-anhydro-1-(3',5'-di-O-acyl-.beta.-D-arabinofuranosyl)pyrimidines from pyrimidine ribonucleosides
  作者：Kazuhiko Kondo、Ichizo Inoue

  DOI：10.1021/jo00437a003

  日期：1977.8
• CHWANG, TEK L.
  作者：CHWANG, TEK L.

  DOI：——

  日期：——