9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-O-(2,4,6-triisopropylbenzenesulfonyl)purine | 119771-85-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-O-(2,4,6-triisopropylbenzenesulfonyl)purine
• 英文别名: O⁶-triisopropylbenzenesulfonyl 3',5'-diacetyldeoxyguanosine；[(2R,3S,5R)-3-acetyloxy-5-[2-amino-6-[2,4,6-tri(propan-2-yl)phenyl]sulfonyloxypurin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 119771-85-6
• 化学式: C₂₉H₃₉N₅O₈S
• 分子量: 617.723
• InChiKey: NLKATSWYBVJKRB-RBZQAINGSA-N

物化性质

• 沸点：
  754.8±70.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-O-(2,4,6-triisopropylbenzenesulfonyl)purine 在 亚硝酸苄基三乙基铵 、 氨 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.08h， 生成 克拉屈滨
  参考文献：
  名称：

  Efficient Syntheses of 2-Chloro-2‘-deoxyadenosine (Cladribine) from 2‘-Deoxyguanosine¹

  摘要：

  We report efficient syntheses of the clinical agent cladribine (2-chloro-2'-deoxyadenosine, CldAdo), which is the drug of choice against hairy-cell leukemia and other neoplasms, from 2'-deoxyguanosine. Treatment of 3',5'-di-O-acetyl- or benzoyl-2'-deoxyguanosine (1) with 2,4,6-triisopropyl- or 4-methylbenzenesulfonyl chloride gave high yields of the 6-O-arylsulfonyl derivatives 2 or 2%. Deoxychlorination at C6 of 1 also proceeded to give the 2-amino-6-chloropurine derivative 5 in excellent yields. The nonaqueous diazotization/chloro dediazoniation (acetyl chloride/benzyltriethylammonium nitrite) of 2, 2%, and 5 gave the 2-chloropurine derivatives 3, 3'b, and 6, respectively. The selective ammonolysis at C6 (arylsulfonate with 3 or chloride with 6) and accompanying deprotection of the sugar moiety gave CldAdo (64-75% overall yield from 1).

  DOI：

  10.1021/jo020644k
• 作为产物：
  描述：

  Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[2-amino-6-(2-trimethylsilanyl-ethoxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 在 4-二甲氨基吡啶 、 叔丁基氯化镁 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-O-(2,4,6-triisopropylbenzenesulfonyl)purine
  参考文献：
  名称：

  Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogues

  摘要：

  Oligonucleotides protected with N-(trimethylsilyiethoxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups were synthesized and deprotected by a single ZnBr2 treatment. Teoc group stabilized dA against depurination. This strategy was applied to the synthesis of base-sensitive oligonucleotide prodrugs bearing S-acetyl-2-thioethyl (Sate) phosphotriesters. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.081

文献信息

• SILYL PROTECTING GROUPS FOR OLIGONUCLEOTIDE SYNTHESIS REMOVED BY A ZnBr₂TREATMENT
  作者：Fernando Ferreira、François Morvan

  DOI：10.1081/ncn-200060342

  日期：2005.4.1

  An oligonucleotide protected with N-(trimethylsilyloxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups was synthesized and deprotected by a single ZnBr2 treatment. Finally it was released from the solid support by cleavage of a disulfide linkage with TCEP. The oligonucleotide was obtained without any basic treatment.

  合成了用 N-(三甲基甲硅烷氧基羰基) (Teoc) 和 P-(三甲基甲硅烷基乙醇) (Tse) 基团保护的寡核苷酸，并通过单一的 ZnBr2 处理脱保护。最后，它通过与 TCEP 的二硫键断裂而从固体支持物上释放出来。寡核苷酸是在没有任何碱性处理的情况下获得的。
• Synthesis of Guanine Derivatives Substituted in the O6-Position by Mitomycin C
  作者：Brian F. McGuinness、Koji Nakanishi、Roselyn Lipman、Maria Tomasz

  DOI：10.1016/s0040-4039(00)80577-8

  日期：——