(3aR)-6c-trimethylsilanyloxy-5t-(trimethylsilanyloxy-methyl)-(3ar,6ac)-3a,5,6,6a-tetrahydro-furo[2,3-d]oxazol-2-ylamine | 58311-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR)-6c-trimethylsilanyloxy-5t-(trimethylsilanyloxy-methyl)-(3ar,6ac)-3a,5,6,6a-tetrahydro-furo[2,3-d]oxazol-2-ylamine
• 英文别名: O²,N-aminomethanylylidene-O³,O⁵-bis-trimethylsilanyl-β-D-arabinofuranosylamine；(3aR,5R,6R,6aS)-6-trimethylsilyloxy-5-(trimethylsilyloxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-2-amine
• CAS: 58311-70-9
• 化学式: C₁₂H₂₆N₂O₄Si₂
• 分子量: 318.52
• InChiKey: WYHFUMXPIXBICV-CHWFTXMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙炔腈 、 (3aR)-6c-trimethylsilanyloxy-5t-(trimethylsilanyloxy-methyl)-(3ar,6ac)-3a,5,6,6a-tetrahydro-furo[2,3-d]oxazol-2-ylamine 以 氘代氯仿 为溶剂， 生成 3c-[(3aR)-2-imino-6c-trimethylsilanyloxy-5t-(trimethylsilanyloxy-methyl)-(3ar,6ac)-tetrahydro-furo[2,3-d]oxazol-3-yl]-acrylonitrile
  参考文献：
  名称：

  An efficient synthesis of 1-.beta.-D-arabinofuranosylcytosine

  摘要：

  DOI：

  10.1021/jo00872a032
• 作为产物：
  描述：

  三甲基氯硅烷 、 阿拉伯糖 、 氰胺 生成 (3aR)-6c-trimethylsilanyloxy-5t-(trimethylsilanyloxy-methyl)-(3ar,6ac)-3a,5,6,6a-tetrahydro-furo[2,3-d]oxazol-2-ylamine
  参考文献：
  名称：

  An efficient synthesis of 1-.beta.-D-arabinofuranosylcytosine

  摘要：

  DOI：

  10.1021/jo00872a032

文献信息

• Chu, Lan Dinh; Hrebabecky, Hubert; Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S129 - S131
  作者：Chu, Lan Dinh、Hrebabecky, Hubert、Holy, Antonin

  DOI：——

  日期：——
• Diastereomeric 5,6-Dihydrothymidines. Preparation, Stereochemical Assignments, and MnO2 Oxidation Studies of Thymidines
  作者：Palle V. P. Pragnacharyulu、Chandra Vargeese、Michael Mc Gregor、Elie Abushanab

  DOI：10.1021/jo00115a026

  日期：1995.5

  A useful method for the stereospecific synthesis of beta-thymidine and beta-5,6-dihydrothymidine nucleosides is described. Condensation of methyl 2-formylpropionate and methyl methacrylate with oxazolines 8 furnished the corresponding 2,2'-anhydrothymidine 11 and a 2:1 diastereomeric mixture of 2,2'-anhydro-5,6-dihydrothymidine 10, respectively. While DDQ oxidation of 10 furnished 11, active MnO2 resulted in a selective dehydrogenation hitherto unreported in nucleoside chemistry. The minor diasteromer 10b was quantitatively converted to 11, leaving 10a unchanged. A plausible explanation for this selectivity was based on the stereochemistry at C5 which was determined by one-dimensional NOE studies.
• .beta.-D-Arabinofuran[1',2':4,5]oxazolo-1,3,5-triazine-5-N-methyl-4,6-dione and analogs, unusually specific immunosuppressive agents
  作者：W. Wierenga、B. E. Loughman、A. J. Gibbons、H. E. Renis

  DOI：10.1021/jm00204a011

  日期：1978.6

  Sequential treatment of the protected beta-D-arabinofuran[1',2':4,5]-2-aminooxazoline (2) with methyl isocyanate and diimidazole carbonyl afforded the 2,2'-anhydro-beta-D-arabinofuranosyl nucleoside, 6. Deprotection and hydrolysis yielded the corresponding arabinoside. Although the anhydronucleoside exhibited in vitro antiviral activity against herpes simplex type 1, it exacerbated the infection in vivo. Further examination uncovered an in vitro inhibition of the induction of a cell-mediated immune response without cytotoxicity.
• An efficient synthesis of 1-.beta.-D-arabinofuranosylcytosine
  作者：Edward J. Hessler

  DOI：10.1021/jo00872a032

  日期：1976.5