methyl 5-bromo-5-deoxy-D-ribofuranoside | 869338-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-bromo-5-deoxy-D-ribofuranoside
• 英文别名: (2S,3S,4R)-2-(bromomethyl)-5-methoxyoxolane-3,4-diol
• CAS: 869338-92-1
• 化学式: C₆H₁₁BrO₄
• 分子量: 227.055
• InChiKey: XDYMFLLJHRJOHK-JDJSBBGDSA-N

物化性质

• 沸点：
  346.3±42.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-bromo-5-deoxy-D-ribofuranoside 、 苯甲酰氯 以75%的产率得到
  参考文献：
  名称：

  RAJU, NATARAJAN;SMEE, DONALD F.;ROBINS, ROLAND K.;VAGHEFI, MORTEZA M., J. MED. CHEM., 32,(1989) N, C. 1307-1313

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 在 硫酸 作用下， 以 甲醇 为溶剂， 以86.0 g的产率得到methyl 5-bromo-5-deoxy-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-.beta.-D-ribofuranosyl analogs of AMP, GMP, IMP, and CMP

  摘要：

  Methyl 2,3-O-isopropylidene-D-ribofuranoside (1) was converted to 1-O-acetyl-5-bromo-5-deoxy-2,3-di-O-benzoyl-D-ribofuranose (6) in five steps with good yield. The Arbuzov condensation of compound 6 with triethyl phosphite resulted in the synthesis of 1-O-acetyl-2,3-di-O-benzoyl-5-deoxy-5-(diethoxyphosphinyl)-D-ribofuranos e (7). Compound 7 was used for direct glycosylation of both purine and pyrimidine bases. The glycosylation was accomplished with the dry silylated heterocyclic base in the presence of trimethylsilyl triflate. Deblocking of the glycosylation products gave exclusively the beta anomer of the 5'-phosphonate analogues of 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]adenine (13), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]guanosin e (16), 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]hypoxant hine (17), and 9-[5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl]cytosine (15), described here for the first time. The target compounds as well as their intermediates showed no in vitro antiviral or antitumor activity, although phosphorylation of 15 and 16 to di- and triphosphate analogues was demonstrated with use of isolated cellular enzymes.

  DOI：

  10.1021/jm00126a027

文献信息

• Pyrrolo-thiazines and processes for the preparation and use thereof
  申请人：Hollingsworth Rawle

  公开号：US20070055062A1

  公开（公告）日：2007-03-08

  1H-Pyrrolo-1,4-thiazines and a process for the preparation thereof are described. These compounds are useful as enzyme inhibitors in cells, particularly for medical uses.

  描述了1H-吡咯并噻嗪及其制备方法。这些化合物在细胞中作为酶抑制剂具有用途，特别适用于医疗用途。
• Design and Evaluation of Dihydroxytetrahydro-1<i>H</i>-pyrrolo[2,1-<i>c</i>]- [1,4]benzothiazines as Conformationally Restricted Transition-State Inhibitors of β-Ribosidases
  作者：Li Gao、Rawle I. Hollingsworth

  DOI：10.1021/jo050374g

  日期：2005.10.1

  The preparation of three new chiral thiazines from ribose is described. Two of these are dihydroxytetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazines with iminopentitol substructures corresponding to the L-Iyxo and D-ribo configurations. They were designed to present a favorable transition-state mimic for the inhibition of ribosidases. This new thiazine class opens the way to the development of new inhibitors to carbohydrate processing enzymes of therapeutic importance such as nucleoside hydrolases and purine nucleoside phosphorylases.
• RAJU, NATARAJAN;SMEE, DONALD F.;ROBINS, ROLAND K.;VAGHEFI, MORTEZA M., J. MED. CHEM., 32,(1989) N, C. 1307-1313
  作者：RAJU, NATARAJAN、SMEE, DONALD F.、ROBINS, ROLAND K.、VAGHEFI, MORTEZA M.

  DOI：——

  日期：——
• PYRROLO-THIAZINES AND PROCESSES FOR THE PREPARATION AND USE THEREOF
  申请人：Michigan State University

  公开号：EP1934232A2

  公开（公告）日：2008-06-25
• US7579343B2
  申请人：——

  公开号：US7579343B2

  公开（公告）日：2009-08-25