methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside | 139212-86-5

• 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-2,3-dideoxy-3-iodo-D-threo-pentofuranoside
• 英文别名: tert-butyl-[[(2R,3R)-3-iodo-5-methoxyoxolan-2-yl]methoxy]-diphenylsilane
• CAS: 139212-86-5
• 化学式: C₂₂H₂₉IO₃Si
• 分子量: 496.46
• InChiKey: UXKSHYKDPPHOAG-OSBQEZSISA-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-2,3-dideoxy-3-iodo-D-threo-pentofuranoside 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 (R)-1-(2,3-dihydro-5-hydroxymethylfuran-2-yl)-5-octyluracil
  参考文献：
  名称：

  Kjaersgaard; Pedersen; Nielsen, Acta Chemica Scandinavica, 1992, vol. 46, # 10, p. 1016 - 1020

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-5-O-tert-butyldiphenylsilyl-2-deoxy-ribo-furanoside 、 碘甲烷 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside
  参考文献：
  名称：

  Convergent synthesis of 2′,3′-dideoxy-3′-methylthio and 2′,3′-dideoxy-3′-mercapto nucleosides and their disulfide analogues — Potential anti-HIV agents

  摘要：

  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.

  DOI：

  10.1007/bf00808508

文献信息

• New Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides.
  作者：Ahmed E. S. Abdel-Megied、Poul Hansen、Erik B. Pedersen、Carsten M. Nielsen、Hugh Brian Dunford、Nils Åge Frøystein、George W. Francis、Britt Karlsson

  DOI：10.3891/acta.chem.scand.45-1060

  日期：——

  The 3'-iodonucleoside 4 and the 3'-O-methylsulfonylthymidine 9 have been synthesized by condensation of silylated uracils 2 with methyl 5-O-tert-butyldiphensilyl-2,3-dideoxy-3-iodo-D-threo-pentofuran oside (3) and methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-methylsulfonyl-D-erythro- pentofuranoside (8), respectively. The nucleoside 4 and 9 produced the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides

  3'-碘核苷4和3'-O-甲基磺酰基胸苷9是通过将甲硅烷基化的尿嘧啶2与5-O-叔丁基二苯甲硅烷基-2,3-二脱氧-3-碘-D-苏-戊呋喃糖苷缩合而合成的（3）和甲基5-O-叔丁基二苯基甲硅烷基-2-脱氧-3-甲基磺酰基-D-季戊基呋喃呋喃糖苷（8）。在用甲醇钠处理的消除反应中，核苷4和9产生了相应的2'，3'-二氢-2'，3'-二脱氧核苷5。化合物5b对HIV-1没有抗病毒活性。
• Synthesis of 3′-Azido, 2′,3′-Didehydro, and 3′,4′-Didehydro Nucleosides from 5-Alkoxymethyluracils
  作者：Ahmed E.-S. Abdel-Megied、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/pl00010110

  日期：1998.1
• El-Barbary, Ahmed A.; El-Brollosy, Nasser R.; Pedersen, Erik B., Bulletin de la Societe Chimique de France, 1996, vol. 133, # 1, p. 51 - 57
  作者：El-Barbary, Ahmed A.、El-Brollosy, Nasser R.、Pedersen, Erik B.

  DOI：——

  日期：——