methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-α-D-threo-pentofuranoside | 130087-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-α-D-threo-pentofuranoside
• 英文别名: tert-butyl-[[(2R,3R,5S)-3-iodo-5-methoxyoxolan-2-yl]methoxy]-diphenylsilane
• CAS: 130087-24-0
• 化学式: C₂₂H₂₉IO₃Si
• 分子量: 496.46
• InChiKey: UXKSHYKDPPHOAG-NJYVYQBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-α-D-threo-pentofuranoside 在 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 乙腈 、 xylene 为溶剂， 反应 4.5h， 生成 1-(3-(2-cyanoethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)uracil
  参考文献：
  名称：

  3-(2-氰乙基)-和3-(2-甲氧羰基乙基)-2,3-二脱氧-α-D-赤型戊呋喃糖苷的自由基合成及其在合成潜在抗病毒核苷中的应用

  摘要：

  在三丁基氢化锡和自由基引发剂 (AIBN) 存在下，不同的碳水化合物离析物 2、5 和 7 与丙烯腈发生自由基反应，得到甲基 3-(2-氰乙基)-2,3-二脱氧戊呋喃糖苷 3a 和 6。 2与丙烯酸甲酯反应得到3-(2-甲氧基羰基乙基>-2,3-二脱氧戊呋喃糖3b。3a与甲硅烷基化尿嘧啶核苷偶联得到β-和α-核苷8和9的异头混合物，脱保护得到10和11，分别。3b 与甲硅烷基化 N4-异丁酰胞嘧啶的类似反应得到 12 和 13，它们被脱保护，分别得到最终的核苷 16 和 17。化合物 10a、11、14-17 都没有显示出显着的抗 HIV 活性。

  DOI：

  10.1002/ardp.2503241203
• 作为产物：
  描述：

  (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran 在 三苯基膦 、 偶氮二甲酸二乙酯 、 碘甲烷 作用下， 生成 methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-α-D-threo-pentofuranoside
  参考文献：
  名称：

  Hansen, Poul; Pedersen, Erik B., Acta Chemica Scandinavica, 1990, vol. 44, # 5, p. 522 - 523

  摘要：

  DOI：

文献信息

• Convergent synthesis of 2′,3′-dideoxy-3′-methylthio and 2′,3′-dideoxy-3′-mercapto nucleosides and their disulfide analogues — Potential anti-HIV agents
  作者：Kim L. Dueholm、Youssef L. Aly、Per T. Jørgensen、Ahmed A. El-Barbary、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808508

  日期：1993.1

  The iodide 4(alpha) or 7 synthesized in three steps from 2-deoxy-D-ribose 1, has been subjected to a number of nucleophilic substitution reactions producing the 3-benzoylthio-, 3-methylthio- and the 3-thiocyanato-2,3-dideoxy-D-erythro-pentofuranosides 8,13 and 15, respectively, in addition to the disulfide 17 of their 3-mercapto analogue. Subjecting the thiobenzoate 8 to the Friedel-Crafts catalyzed silyl Hilbert Johnson reaction in conjunction with the silylated nucleobases of uracil, thymine and N4-isobutyrylcytosine 9a-c resulted in the isolation of the 2',3'-dideoxy-3'-mercapto nucleosides 11 and their disulfides 12 subsequent to deprotection. The 2,3-dideoxy-3-methylthio-pentofuranoside 13 afforded both anomers of the 2',3'-dideoxy-3'-methylthio nucleosides 19 and 20 under similar conditions. The first known example of a coupling directly on a 2,3-didehydro-2,3-dideoxyfuranose is presented. 2',3'-Dideoxy-3'-mercaptocytidine showed protection against HIV-1 in MT-4 cells with ED50 = 20 muM.
• Convergent synthesis of 2?,3?-dideoxy-3?-mercapto nucleosides ? Potential anti-HIV agents
  作者：A. A. El-Barbary、A. I. Khodair、E. B. Pedersen、C. Nielsen

  DOI：10.1007/bf00812717

  日期：——

  Methyl 3-benzoylthio-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-beta-D- erythro-pentofuranoside (4) and its corresponding alpha anomer 5 were synthesized in four steps from 2-deoxy-D-ribose and used as substrates for the synthesis of nucleosides by condensation with silylated thymidine and N-6-isobutyryladenine. The nucleosides were deprotected by treatment with Bu(4)NF in THF followed by reaction with MeONa in MeOH to give 3'-deoxy-3'-mercaptothymidine (8), 2',3'-dideoxy-3'mercaptoadenosine (15) and its corresponding alpha anomer 16. In the latter reactions it was important to use degassed solvents to minimize formation of the corresponding disulfides of purine nucleosides. Using Bu(4)NF, without subsequent reaction with MeONa in the deprotection reaction, resulted in intermolecular transesterification reactions.
• Walczak, Krzysztof; Pupek, Krzysztof; Pedersen, Erik B., Liebigs Annalen der Chemie, 1991, # 10, p. 1041 - 1044
  作者：Walczak, Krzysztof、Pupek, Krzysztof、Pedersen, Erik B.

  DOI：——

  日期：——
• HANSEN, POUL;PEDERSEN, ERIK B., ACTA CHEM. SCAND., 44,(1990) N, C. 522-523
  作者：HANSEN, POUL、PEDERSEN, ERIK B.

  DOI：——

  日期：——