1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine | 129778-51-4

• 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-β-D-erythro-pentofuranosyl>thymine
• 英文别名: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine；1-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythropentofuranosyl]thymine；1-[5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl]thymine；PhS(-2d)[TBDPS(-5)]3-deoxy-D-eryPenf(b)-thymin-1-yl；1-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylsulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 129778-51-4
• 化学式: C₃₂H₃₆N₂O₄SSi
• 分子量: 572.8
• InChiKey: MHVVUFOXKOSVLB-PDVBFRJSSA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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

• 作为反应物：
  描述：

  1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine 在 吡啶 、 sodium periodate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 司他夫定
  参考文献：
  名称：

  控制2'-脱氧核糖核苷合成中糖基化立体化学的一般方法

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)98793-8
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 四氯化锡 4-二甲氨基吡啶 、 二异丁基氢化铝 、 lithium cyclohexylisopropylamide 作用下， 以 四氢呋喃 、 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-β-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

• PROCESS FOR PRODUCING NUCLEOSIDE DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0598910A1

  公开（公告）日：1994-06-01

  A process for producing a nucleoside derivative (1) by reacting a substituted 2,3-dihydrofuran derivative (2) with an organohalogen compound (3) containing a group 16 element of the periodic table to give a substituted 2- halotetrahydrofuran derivative (4), condensing the derivative (4) with a nucleic acid base to give a substituted nucleoside derivative (5), and reducing the derivative (5), wherein R1 represents hydrogen, alkyl or R6-O-CH2-; R2 to R4 represent each hydrogen or a group containing a group 14-17 element of the periodic table; R5 represents optionally substituted alkyl or phenyl; A represents a group 16 element of the periodic table; B represents a nucleic acid base; and X represents halogen.

  通过将取代的2,3-二氢呋喃衍生物（2）与含周期表第16族元素的有机卤化物（3）反应，从而得到取代的2-卤代四氢呋喃衍生物（4），将衍生物（4）与核酸碱基缩合以得到取代的核苷衍生物（5），并还原衍生物（5），从而生产核苷衍生物（1）的方法，其中R1代表氢、烷基或R6-O-CH2-；R2到R4分别代表氢或含周期表第14-17族元素的基团；R5代表可选择地取代的烷基或苯基；A代表周期表第16族元素；B代表核酸碱基；X代表卤素。
• 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：——