(3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole | 73111-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole
• 英文别名: (3aR,4R,5S,6S,6aR)-1-methyl-4,5,6-tris(phenylmethoxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[c][1,2]oxazole
• CAS: 73111-18-9
• 化学式: C₂₈H₃₁NO₄
• 分子量: 445.558
• InChiKey: YWGHQAUCYFKZTO-WMJDNDCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole 在 sodium tetrahydroborate 、 溶剂黄146 、 nickel dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol
  参考文献：
  名称：

  Conformationally Biased Mimics of Mannopyranosylamines: Inhibitors of β-Mannosidases?

  摘要：

  The enol ether 7 was prepared by cleavage of the N-O bond of the known isoxazolidine 3, followed by N-alkylation to 4, silylation and oxidation to the N-oxide 6, and Cope elimination. Cu-Catalysed cyclopropanation of 7 led to the diastereoisomeric cyclopropanes 8 and 9, which were subjected to a Curtius degradation, The resulting carbamates 12 and 16 were deprotected to the ammonium salts 14 and 18, respectively. Both salts adopt a B-1,B-4 conformation, similarly as the ester 8, while the isomeric ester 9 exists in a ca, 6:4 equilibrium of the C-4(1) and B-1,B-4 conformers. The beta-mannoside mimic 14 does not inhibit snail beta-mannosidase at 10 mM, but the alpha-mannoside mimic 18 inhibits Jack bean alpha-mannosidase (IC50 = 80 muM). These results are in keeping with the postulate that glycoside cleavage of beta-D-glycopyranosides requires a conformational change in agreement with the principle of stereoelectronic control.

  DOI：

  10.1002/1522-2675(200204)85:4<1118::aid-hlca1118>3.0.co;2-s
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 methyl tri-O-benzyl-6-bromo-β-D-6-deoxy-glucopyranoside 生成 (3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole
  参考文献：
  名称：

  Carbocyclische Verbindungen aus单糖。I. Umsetzungen在葡萄糖中

  摘要：

  来自单糖的碳环化合物。1.葡萄糖系列的转变

  DOI：

  10.1002/hlca.19790620629