1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose | 812644-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose
• 英文别名: [(2R)-2-acetoxy-2-[(2R,3R,4R)-3,4,5-triacetoxytetrahydrofuran-2-yl]ethyl] acetate；[(2R)-2-acetyloxy-2-[(2R,3R,4R)-3,4,5-triacetyloxyoxolan-2-yl]ethyl] acetate
• CAS: 812644-06-7
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: JRZQXPYZEBBLPJ-XIHUBIEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose 在 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 2-amino-9-[(2R,3R,4S,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxytetrahydrofuran-2-yl]-1H-purin-6-one
  参考文献：
  名称：

  [EN] NOVEL LIGANDS FOR ASIALOGLYCOPROTEIN RECEPTOR
  [FR] NOUVEAUX LIGANDS POUR LE RÉCEPTEUR D'ASIALOGLYCOPROTÉINE

  摘要：

  公开号：

  WO2022084331A3
• 作为产物：
  描述：

  3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 吡啶 、 硫酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 36.0h， 生成 1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose
  参考文献：
  名称：

  [EN] NOVEL LIGANDS FOR ASIALOGLYCOPROTEIN RECEPTOR
  [FR] NOUVEAUX LIGANDS POUR LE RÉCEPTEUR D'ASIALOGLYCOPROTÉINE

  摘要：

  公开号：

  WO2022084331A3

文献信息

• An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs
  作者：Audrey Hospital、Maïa Meurillon、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1021/ol402143y

  日期：2013.9.20

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.
• New Nucleoside−Sugar Conjugates:  6-<i>N</i>-Glycosyloxyphosphorylated Adenosine Derivatives as Partial Structures of Agrocin 84
  作者：Tomohisa Moriguchi、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo961489a

  日期：1996.1.1

  We report the first successful synthesis of 6-N-[(glucofuranos-1-yloxy)phosphoryl]adenosine as a partial structure of Agrocin 84 via a two-step phosphorylation of 2',3',5'-tri-O-benzoyladenosine with a 2,3,5,6-tetra-O-acetylglucofuranoside 1-O-phosphoramidite derivative that has a 2-(trimethylsilyl)ethyl group as the phosphate protecting group. A similar nucleoside-sugar conjugate, 6-N-[(ribofuranos-1-yloxy)phosphoryl]ade was also synthesized. The stabilities of these 6-N-[(glycos-1-yloxy)phosphoryl] adeno sine derivatives under acidic, basic, and thermal conditions are described. In particular, we found that the P-O bond of these sugar-nucleoside conjugates was selectively cleaved by treatment with 0.1 M NaOH to give 6-N-phosphoryladenosine, while acidic treatment gave directly adenosine with cleavage of the P-N bond.
• Inactivation of human S-adenosylhomocysteine hydrolase by covalent labeling of cysteine 195 with thionucleoside derivatives
  作者：Georges Guillerm、Murielle Muzard、Cédric Glapski、Serge Pilard

  DOI：10.1016/j.bmcl.2004.09.051

  日期：2004.12

  -A new series of 5'-thioadenosine derivatives 1-4 were synthesized for selectively targeting (CYS)-C-195 of human AdoHcy hydrolase. Their incubation with the enzyme resulted in time- and concentration-dependent inactivation, without major modifications of the NAD(+)/NADH ratio. The electrospray mass analysis of the inactivated enzyme with 1, 2, 3, and 4b showed that inhibition was accompanied by the formation of a specific and covalent labeling of each AdoHcy hdrolase subunit. Proteolytic cleavage (endo-Lys-C) and subsequent peptide characterization of the labeled enzyme revealed that (195)Cys was the residue modified during the inactivation process. (C) 2004 Elsevier Ltd. All rights reserved.