benzyl N-[(1R,2R,3S,4R,5S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxycyclopentyl]carbamate | 205649-25-8

• 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: benzyl N-[(1R,2R,3S,4R,5S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxycyclopentyl]carbamate
• CAS: 205649-25-8
• 化学式: C₃₈H₇₅NO₇Si₄
• 分子量: 770.358
• InChiKey: PLPZDLBPRXDYRI-IIQKAQNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.22
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1R,2R,3S,4R,5S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxycyclopentyl]carbamate 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 N-<2-<<1R-(1α,2β,3α,4β,5β)>-(1-hydroxymethyl-1,2,3,4-tetrahydroxycyclopent-5-yl)aminothiocarbonyl>aminoethyl>-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Syntheses of 1-deoxynojirimycin-trehalamine-fused and -linked compounds and their biological activities

  摘要：

  1-Deoxynojirimycin-trehalamine-fused and -linked compounds (10, 19a and 19b) were synthesized from 1-deoxy-2,3,4,6-tetra-O-benzylnojirimycin and trehazolamine, which was obtained from natural trehazorin as a degradation product. None of these synthetic compounds exceeded 1-deoxynojirimycin in the inhibitory activities towards rat intestinal maltase and yeast alpha-D-glucosidase. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00966-1
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 112.0h， 生成 benzyl N-[(1R,2R,3S,4R,5S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxycyclopentyl]carbamate
  参考文献：
  名称：

  Syntheses of 1-deoxynojirimycin-trehalamine-fused and -linked compounds and their biological activities

  摘要：

  1-Deoxynojirimycin-trehalamine-fused and -linked compounds (10, 19a and 19b) were synthesized from 1-deoxy-2,3,4,6-tetra-O-benzylnojirimycin and trehazolamine, which was obtained from natural trehazorin as a degradation product. None of these synthetic compounds exceeded 1-deoxynojirimycin in the inhibitory activities towards rat intestinal maltase and yeast alpha-D-glucosidase. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00966-1

文献信息

• Synthesis of 1-deoxynojirimycin-trehalamine fused compound and its related compounds
  作者：Masao Shiozaki、Osamu Ubukata、Hideyuki Haruyama、Reiko Yoshiike

  DOI：10.1016/s0040-4039(98)00049-5

  日期：1998.4

  1-Deoxynojirimycin-trehalamine fused compound 10 as a mixture together with 11 and its related compound 19 were synthesized The enzyme inhibitory activities of the mixture (10 and 11), 19 and 20 exhibited IC50 values of 0.68, 4.2, and 1.5 mu g/ml, respectively, toward rat intestinal maltase. (C) 1998 Elsevier Science Ltd. All rights reserved.