1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol | 73111-43-0

• 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: 1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol
• CAS: 73111-43-0
• 化学式: C₂₉H₃₅NO₄
• 分子量: 461.601
• InChiKey: YAOFQOTVFVLJLD-ZKZHHWRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol 在 铜 咪唑 、 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 3,4,5-tri-O-benzyl-2,6-dideoxy-2,6-methylene-D-glycero-D-gulo-3,6a-cycloheptonic acid
  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：

  (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

文献信息

• Carbocyclische Verbindungen aus Monosacchariden. I. Umsetzungen in der glucosereihe
  作者：Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.19790620629

  日期：1979.9.19

  Carbocyclic Compounds from Monosaccharides. 1. Transformations in the Glucose Series

  来自单糖的碳环化合物。1.葡萄糖系列的转变