9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-iodo-9H-purin-6-ylamine | 114763-43-8

• 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-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-iodo-9H-purin-6-ylamine
• 英文别名: 9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-iodopurin-6-amine
• CAS: 114763-43-8
• 化学式: C₂₈H₅₄IN₅O₄Si₃
• 分子量: 735.929
• InChiKey: UPOUYDOBRVKTQT-UMCMBGNQSA-N

物化性质

• 沸点：
  650.2±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-iodo-9H-purin-6-ylamine 生成 1-{6-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-2-yl}-propan-2-one
  参考文献：
  名称：

  NAIR, VASU;TURNER, GREGORY A.;BUENGER, GREG S.;CHAMBERLAIN, STANLEY D., J. ORG. CHEM., 53,(1988) N 13, 3051-3057

  摘要：

  DOI：
• 作为产物：
  描述：

  2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 咪唑 、 二碘甲烷 、 亚硝酸正戊酯 、 氨 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 生成 9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-iodo-9H-purin-6-ylamine
  参考文献：
  名称：

  New methodologies for the synthesis of C-2 functionalized hypoxanthine nucleosides

  摘要：

  DOI：

  10.1021/jo00248a027

文献信息

• A New Entry to 2-Substituted Purine Nucleosides Based on Lithiation-Mediated Stannyl Transfer of 6-Chloropurine Nucleosides
  作者：Keisuke Kato、Hiroyuki Hayakawa、Hiromichi Tanaka、Hiroki Kumamoto、Satoru Shindoh、Satoshi Shuto、Tadashi Miyasaka

  DOI：10.1021/jo970398q

  日期：1997.10.1

  In spite of exclusive lithiation at the 8-position of 9-(2,3,5-tris-O-TBDMS-beta-D-ribofuranosyl)-6-chloropurine (2) with LDA, subsequent quenching of its lithiated species with Bu3SnCl (or TMSCl) results in the formation of 2-substituted products. Under optimized reaction conditions, where LTMP was us ed as a lithiating agent, 9-(2,3,5-tris-O-TBDMS-beta-D-ribofuranosyl)-6-chloro-2-(tributylstannyl)purine (11) was formed in quantitative yield. Several experiments carried out to verify the reaction mechanism suggested that an anionic stannyl (or silyl) transfer from the 8- to the 2-position had been involved. Manipulation of the 2-tributylstannyl group in 11 and in its adenine counterpart (22) has disclosed a new entry to 2-substituted purine nucleosides. This chemistry was briefly applied to the synthesis of the 2-fluoro analogue of neplanocin A.
• Copper mediated reactions in nucleoside synthesis
  作者：Vasu Nair、Todd B Sells

  DOI：10.1016/s0040-4039(00)94633-1

  日期：1990.1
• NAIR, VASU;SELLS, TODD B., TETRAHEDRON LETT., 31,(1990) N, C. 807-810
  作者：NAIR, VASU、SELLS, TODD B.

  DOI：——

  日期：——