Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-amino-purin-9-yl)-5-((2-cyano-ethoxy)-{(S)-1-methyl-2-[(2S,3R,4R,5R,6R)-3,4,5-triacetoxy-6-((R)-1,2-diacetoxy-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester | 933037-75-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-amino-purin-9-yl)-5-((2-cyano-ethoxy)-{(S)-1-methyl-2-[(2S,3R,4R,5R,6R)-3,4,5-triacetoxy-6-((R)-1,2-diacetoxy-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester
• CAS: 933037-75-3
• 化学式: C₃₇H₄₉N₆O₂₀P
• 分子量: 928.798
• InChiKey: NKFPEHQNWDWOGS-HSGPYOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  340.73
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-amino-purin-9-yl)-5-((2-cyano-ethoxy)-{(S)-1-methyl-2-[(2S,3R,4R,5R,6R)-3,4,5-triacetoxy-6-((R)-1,2-diacetoxy-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester 、 三乙胺 以 甲醇 、 水 为溶剂， 反应 3.0h， 以53%的产率得到triethylammonium adenosine 5'-(4,8-anhydro-1,3-dideoxy-D-ribo-L-manno-decit-2-yl)phosphate
  参考文献：
  名称：

  Synthesis of C-glycosidically linked ADP glycero-β-d-manno-heptose analogues

  摘要：

  C-Glycosides Of L-glycero-D-manno- and D-glycero-D-manno-heptose containing either (S)- or (R)-2-hydroxypropyl aglycons are easily accessible compounds via condensation of reducing heptoses with pentane-2,4-dione. 2%3'-Di-O-acetyl adenosine was transformed into the corresponding 5'-O-cyanoethyl N,N-diisopropylaminophosphoramidite derivative, which was coupled in fair yields to the O-acetylated diastereoisomeric C-glycosidic alcohols. Oxidation of the phosphite triesters followed by deprotection furnished four ADP-heptose analogues, wherein the heptosyl phosphate moiety had been replaced by a three carbon-skeleton. The compounds serving as substrate analogues will be used for co-crystallization experiments with ADP heptosyl transferases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.015
• 作为产物：
  描述：

  2-cyanoethyl-[5'-O-(2',3'-di-O-acetyl)adenosine]-N,N-diisopropylaminophosphine 在 四氮唑 、 二叔丁基过氧化物 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-amino-purin-9-yl)-5-((2-cyano-ethoxy)-{(S)-1-methyl-2-[(2S,3R,4R,5R,6R)-3,4,5-triacetoxy-6-((R)-1,2-diacetoxy-ethyl)-tetrahydro-pyran-2-yl]-ethoxy}-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of C-glycosidically linked ADP glycero-β-d-manno-heptose analogues

  摘要：

  C-Glycosides Of L-glycero-D-manno- and D-glycero-D-manno-heptose containing either (S)- or (R)-2-hydroxypropyl aglycons are easily accessible compounds via condensation of reducing heptoses with pentane-2,4-dione. 2%3'-Di-O-acetyl adenosine was transformed into the corresponding 5'-O-cyanoethyl N,N-diisopropylaminophosphoramidite derivative, which was coupled in fair yields to the O-acetylated diastereoisomeric C-glycosidic alcohols. Oxidation of the phosphite triesters followed by deprotection furnished four ADP-heptose analogues, wherein the heptosyl phosphate moiety had been replaced by a three carbon-skeleton. The compounds serving as substrate analogues will be used for co-crystallization experiments with ADP heptosyl transferases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.015