1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine | 132336-18-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine
• 英文别名: 1-[5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl]thymine；PhS(-2d)[TBDPS(-5)]3-deoxy-D-eryPenf(a)-thymin-1-yl；1-[(2S,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 132336-18-6
• 化学式: C₃₂H₃₆N₂O₄SSi
• 分子量: 572.8
• InChiKey: MHVVUFOXKOSVLB-XGSJXSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-ol 在 四氯化锡 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Stereoselectivity in the Coupling Reaction between 2-Phenylthio-2,3-dideoxyribose and Silylated Pyrimidine Bases

  摘要：

  在SnCl4存在下，2-α-苯硫基-2,3-双脱氧核糖与硅化嘧啶碱基的耦合反应以立体选择性方式进行，得到β-异构体。这些核苷随后通过氧化后进行热消除，转化为2′,3′-双脱氧-2′,3′-双脱氢核苷。

  DOI：

  10.1246/cl.1990.1459

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。
• Stereocontrolled glycosylations via additions of sulfur electrophiles to glycals
  作者：Jianying Wang、Julie A. Wurster、Lawrence J. Wilson、Dennis Liotta

  DOI：10.1016/s0040-4039(00)74036-6

  日期：1993.7

  The methodology described herein examines the regio- and stereoselectivity of pyrimidine and purine glycosylations of furanoid glycals. The results show that following stereoselective sulfenylation, glycosylation of furanoid glycals, in the presence of SnCl4, Proceeds both regio- and stereoselectively.
• Furanoid Glycal as a Starting Material for Nucleoside Derivatives
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Koji Okano、Katsuya Matsumoto、Hajime Matsushita

  DOI：10.3987/com-93-6503

  日期：——

  Furanoid glycal was utilized as a starting material for the nucleoside derivatives with the aid of benzenesulfenyl chloride. Condensation reaction with silylated nucleic bases was high in the presence of SnCl4. Electrophilic addition of benzenesulfenyl chloride to the glycal with substituent also proceeded in high stereoselectivity. Phenylthio-substituted nucleoside was used to convert 2',3'-dideoxynucleoside and 2',3'-didehydro-2',3'-dideoxynucleoside.
• Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides Utilizing Coupling Reactions between Nucleic Bases and Phenylthio-substituted 2,3-Dideoxyribose
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Katsuya Matsumoto、Hajime Matsushita、Yoshitake Naoi、Kazuo Ito

  DOI：10.3987/com-91-5884

  日期：——

  Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-alpha-phenylthio-2,3-dideoxyribose were examined. In the former case, no stereoselectivies were observed when the coupling reactions were performed either with 1-chlorosugar in an S(N)2 mode or in the presence of Lewis acids as catalyst in an S(N)1 mode. Coupling reaction with 2-alpha-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of alpha:beta = 1:9. All these nucleosides were converted to 2',3'-didehydro-2',3'-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.
• KAWAKAMI, HIROSHI;EBATA, TAKASHI;KOSEKI, KOSHI;MATSUSHITA, HAJIME;NAOI, Y+, CHEM. LETT.,(1990) N, C. 1459-1462
  作者：KAWAKAMI, HIROSHI、EBATA, TAKASHI、KOSEKI, KOSHI、MATSUSHITA, HAJIME、NAOI, Y+

  DOI：——

  日期：——