<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> | 141684-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>
• 英文别名: <1-<2',5'-bis-O-(t-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole-2'',2''-dioxide>；1-[(5S,6R,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2lambda6-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4-dione；1-[(5S,6R,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2λ6-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4-dione
• CAS: 141684-45-9
• 化学式: C₂₄H₄₃N₃O₈SSi₂
• 分子量: 589.858
• InChiKey: YMSLYTIPSGCZRM-DUFJIPPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 生成 1-[(5S,6R,8R)-4-Amino-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dioxo-1,7-dioxa-2λ⁶-thia-spiro[4.4]non-3-en-8-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  TSAO Derivatives: Highly Specific Inhibitors of Human Immunodeficiency Virus Type-1 (HIV-1) Replication

  摘要：

  TSAO derivatives represent a unique class of nucleosides that are specifically targeted at HIV-1 RT. This overview is focussed on the chemical synthesis, the conformational studies, the antiviral and metabolic properties of TSAO derivatives, as well as their mechanism of antiviral action and the molecular basis of the vapid selection of resistant HIV-1 strains that emerge in cell culture in the presence of TSAO derivatives.

  DOI：

  10.1080/15257779508012432
• 作为产物：
  描述：

  1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-xylofuranosyl>thymine 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以87%的产率得到<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>
  参考文献：
  名称：

  3'-螺旋核苷，一类新型的特定类型的人类免疫缺陷病毒1型抑制剂：[2'-5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-木糖和-呋喃核糖的合成和抗病毒活性-3'-螺-5“-[4”-氨基-1“，2”-草硫醇2“，2”-二氧化物]（TSAO）嘧啶核苷。

  摘要：

  已经合成了一系列的3'-螺核苷，并被评估为抗HIV-1药物。呋喃糖-3'-核糖基核苷酸的O-甲磺酰基氰醇与碱反应，得到[1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-二甲苯基和-呋喃呋喃糖基]]-3'胸腺嘧啶，尿嘧啶和4-N-乙酰胞嘧啶11和12的-spiro-5“-[4”-氨基-1“，2”-草硫醇2“，2”-二氧化物]衍生物11和12的甲硅烷基化可得到全部去保护的3'-螺木糖核糖核苷酸和核呋喃糖基核苷13和14或部分5'-O-去保护的3'-螺β-D-木糖和核糖核苷15和16，或2'-O-去保护的- 3′-螺β-D-核糖核苷17。17的2′-脱氧得到2′-脱氧-3′-螺β-D-赤型-五呋喃糖基衍生物18。这3′。评价了螺-螺衍生物的抗HIV-1活性。具有木糖构型的所有3'-螺核苷均未显示出任何抗HIV-1活性。在C-2'或C-5'处没有或仅有一个甲硅烷基或2'-脱氧衍生物的

  DOI：

  10.1021/jm00093a002

文献信息

• Synthesis of {1-[2′,5′-Bis-O-(t-butyldimethylsilyl)-β-d-xylo- and β-d-ribofuranosyl]thymine}-3′-spiro-5″-{4″-amino-1″,2″-oxathiole-2″,2″-dioxide} (TSAO). A novel type of specific anti-HIV agents
  作者：María-Jesús Pérez-Pérez、Ana San-Félix、Camarasa María-José、Jan Balzarini、de Clercq Erik

  DOI：10.1016/s0040-4039(00)79591-8

  日期：1992.5

  Reaction of O-mesylcyanohydrins of furanos-3′-ulosyl thymine with bases afforded β-d-xylo- and ribo-3′-substituted nucleosides. 2′-Deoxygenation of the selectively 5′-O-protected nucleoside gave the ribofuranosyl derivative of thymidine.

  呋喃糖-3'-磺基胸腺嘧啶的O-甲磺酰基氰醇与碱反应，得到β-d-木糖基和核糖-3'-取代的核苷。选择性5'-O-保护的核苷的2'-脱氧得到胸苷的核呋喃糖基衍生物。
• 3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2', 5'-bis-O-(tert-butyldimethylsilyl)-.beta.-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino-1'', 2''-oxathiole 2'', 2''-dioxide] (TSAO) pyrimidine nucleosides
  作者：Maria Jose Camarasa、Maria Jesus Perez-Perez、Ana San-Felix、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00093a002

  日期：1992.7

  A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesylcyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1-[2',5'-bis-O- (tert-butyldimethylsilyl)-beta-D-xylo- and -ribofuranosyl]]-3'-spiro-5"- [4"-amino-1",2"-oxathiole 2",2"-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave

  已经合成了一系列的3'-螺核苷，并被评估为抗HIV-1药物。呋喃糖-3'-核糖基核苷酸的O-甲磺酰基氰醇与碱反应，得到[1- [2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-二甲苯基和-呋喃呋喃糖基]]-3'胸腺嘧啶，尿嘧啶和4-N-乙酰胞嘧啶11和12的-spiro-5“-[4”-氨基-1“，2”-草硫醇2“，2”-二氧化物]衍生物11和12的甲硅烷基化可得到全部去保护的3'-螺木糖核糖核苷酸和核呋喃糖基核苷13和14或部分5'-O-去保护的3'-螺β-D-木糖和核糖核苷15和16，或2'-O-去保护的- 3′-螺β-D-核糖核苷17。17的2′-脱氧得到2′-脱氧-3′-螺β-D-赤型-五呋喃糖基衍生物18。这3′。评价了螺-螺衍生物的抗HIV-1活性。具有木糖构型的所有3'-螺核苷均未显示出任何抗HIV-1活性。在C-2'或C-5'处没有或仅有一个甲硅烷基或2'-脱氧衍生物的
• TSAO Derivatives: Highly Specific Inhibitors of Human Immunodeficiency Virus Type-1 (HIV-1) Replication
  作者：Maria Camarasa、Maria Péarez-Péarez、Sonsoles Velázquez、Ana San-Féalix、Rosa Alvarez、Simon Ingate、Maria Luisa Jimeno、Anna Karlsson、Erik De Clercq、Jan Balzarini

  DOI：10.1080/15257779508012432

  日期：1995.5.1

  TSAO derivatives represent a unique class of nucleosides that are specifically targeted at HIV-1 RT. This overview is focussed on the chemical synthesis, the conformational studies, the antiviral and metabolic properties of TSAO derivatives, as well as their mechanism of antiviral action and the molecular basis of the vapid selection of resistant HIV-1 strains that emerge in cell culture in the presence of TSAO derivatives.