(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan | 125440-13-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan
• 英文别名: tert-butyl-diphenyl-[[(2S)-5-trimethylsilyloxy-2,3-dihydrofuran-2-yl]methoxy]silane
• CAS: 125440-13-3
• 化学式: C₂₄H₃₄O₃Si₂
• 分子量: 426.703
• InChiKey: XVPUYHSMKWKICE-FQEVSTJZSA-N

物化性质

• 沸点：
  444.5±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 在 吡啶 、 4-二甲氨基吡啶 、 ammonium sulfate 、 三乙基硼 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 二异丁基氢化铝 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 8.75h， 生成 2,3-二脱氧胞啶
  参考文献：
  名称：

  A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides

  摘要：

  A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

  DOI：

  10.1021/jo00040a031
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 咪唑 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan
  参考文献：
  名称：

  A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides

  摘要：

  A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

  DOI：

  10.1021/jo00040a031

文献信息

• A general method for controlling glycosylation stereochemistry in the synthesis of 2′-deoxyribose nucleosides
  作者：Lawrence J. Wilson、Dennis Liotta

  DOI：10.1016/s0040-4039(00)98793-8

  日期：1990.1

  Glycosylation reactions of 2-arylsulfinyl-O-acetylribosides6 with silylated thymine11 produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T,2, is described.

  2-芳基亚磺酰基-O-乙酰基核糖苷6与甲硅烷基化的胸腺嘧啶11的糖基化反应产生具有高β-选择性的2'-脱氧核糖核苷。描述了这种指导作用在抗逆转录病毒药D4T，2的合成中的应用。
• Synthesis of [4-(hydroxy)tetrahydrofuran-2-yl]nucleosides as a novel class of uridine phosphorylase inhibitors
  作者：Te-Fang Yang、Lakshmi P. Kotra、Quincy Teng、Fardos N.M. Naguib、Jean-Pierre Sommadossi、Mahmoud el Kouni、Chung K. Chu

  DOI：10.1016/0040-4039(94)02421-7

  日期：1995.2

  [4-(Hydroxy)tetrahydrofuran-2-yl]thymine was synthesized and found to be a potent inhibitor of uridine phosphorylase.

  合成了[4-（羟基）四氢呋喃-2-基]胸腺嘧啶，发现它是尿苷磷酸化酶的有效抑制剂。
• A highly stereoselective glycosylation of 2-(phenylselenenyl)-2,3-dideoxyribose derivative with thymine: synthesis of 3'-deoxy-2',3'-didehydrothymidine and 3'-deoxythymidine
  作者：Chung K. Chu、J. Ramesh Babu、J. Warren Beach、Soon K. Ahn、Haoqiang Huang、Lak S. Jeong、Sang J. Lee

  DOI：10.1021/jo00292a006

  日期：1990.3
• Diastereoselective sulfenylation reactions employing N-phenylthio lactams under nonbasic conditions
  作者：Lawrence J. Wilson、Dennis C. Liotta

  DOI：10.1021/jo00033a004

  日期：1992.3

  Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones.