(5R,6R,7R,8R)-6,7-di-O-acetyl-8-acetoxymethyl-1-aza-3-oxabicyclo[3.3.0]octan-2-one | 534573-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5R,6R,7R,8R)-6,7-di-O-acetyl-8-acetoxymethyl-1-aza-3-oxabicyclo[3.3.0]octan-2-one
• 英文别名: [(5R,6R,7R,7aR)-6,7-diacetyloxy-3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-yl]methyl acetate
• CAS: 534573-33-6
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: YASHYRNQPBJTGL-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5R,6R,7R,8R)-6,7-di-O-acetyl-8-acetoxymethyl-1-aza-3-oxabicyclo[3.3.0]octan-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-Dihydroxy-2-hydroxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester 在 ruthenium trichloride 4-二甲氨基吡啶 、 sodium periodate 、 锂硼氢 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 15.25h， 生成 (5R,6R,7R,8R)-6,7-di-O-acetyl-8-acetoxymethyl-1-aza-3-oxabicyclo[3.3.0]octan-2-one
  参考文献：
  名称：

  Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

  摘要：

  cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00017-0