[2R-(2α,3α,4β,5α,6β)]-3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl)-2-piperidinemethanol | 137326-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [2R-(2α,3α,4β,5α,6β)]-3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl)-2-piperidinemethanol
• 英文别名: [(2R,3S,4R,5R,6R)-1-benzyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-2-yl]methanol
• CAS: 137326-11-5
• 化学式: C₄₂H₄₅NO₅
• 分子量: 643.823
• InChiKey: VJWNQPQYMIAZJI-QBLDGPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2R-(2α,3α,4β,5α,6β)]-3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl)-2-piperidinemethanol 在 4-二甲氨基吡啶 、 草酰氯 、 dimethyl sulfide borane 、 双氧水 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， 生成 Benzoic acid 1-((2R,3S,4S,5R,6R)-1-benzyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-piperidin-2-yl)-4-hydroxy-butyl ester
  参考文献：
  名称：

  Synthesis of polyhydroxylated indolizidine and quinolizidine compounds--potent inhibitors of α-glucosidase I

  摘要：

  Polyhydroxylated indolizidine 6a and quinolizidine 6b were synthesized from a common precursor, iminoheptitol 8. The target compounds are potent inhibitors of the glycoprotein trimming enzyme--alpha-glucosidase I.

  DOI：

  10.1016/s0040-4039(00)79409-3
• 作为产物：
  描述：

  2,6-dideoxy-2,6-<<(phenylmethoxy)carbonyl>imino>-1,3,4,5-tetrakis-O-(phenylmethyl)-D-glycero-L-gulo-heptitol 在 palladium on activated charcoal aluminium hydride 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [2R-(2α,3α,4β,5α,6β)]-3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl)-2-piperidinemethanol
  参考文献：
  名称：

  Synthesis of polyhydroxylated indolizidine and quinolizidine compounds--potent inhibitors of α-glucosidase I

  摘要：

  Polyhydroxylated indolizidine 6a and quinolizidine 6b were synthesized from a common precursor, iminoheptitol 8. The target compounds are potent inhibitors of the glycoprotein trimming enzyme--alpha-glucosidase I.

  DOI：

  10.1016/s0040-4039(00)79409-3

文献信息

• Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes
  作者：Yves Blériot、Tao Liu、Yongmin Zhang

  DOI：10.1055/s-2007-973884

  日期：2007.4

  N-Benzyl pentahydroxyazepanes undergo ring isomerization during mesylation of the hydroxyl group β to the nitrogen via a neighboring nitrogen participation involving a transient aziridinium species which is trapped by chlorine. The resulting chloro­methyl tetrahydroxypiperidines have been converted into the corresponding homoglyconojirimycins.

  N-苄基五羟基氮杂环庚烷在对氮原子的β羟基进行梅斯化时，会经历环异构化，涉及一个邻近氮原子的参与，形成一个短暂的氮杂环烷类中间体，该中间体被氯捕获。最终得到的氯甲基四羟基哌啶已被转化为相应的同糖酸酶抑制剂。
• Hydroxymethyl-indolizidines and quinolizidines and their use as
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05028614A1

  公开（公告）日：1991-07-02

  The present invention describes a group of polyhydroxylated indolizidines and quinolizidines and their esters. These compounds are prepared starting from 2,6-dideoxy-2,6-dideoxy-2,6-imino-1,3,4,5-tetrakis-O- (phenylmethyl)-D-glycero-L-gulo-heptitol or a corresponding N-substituted compound. The compounds are useful in the treatment of diabetes and as .alpha.-glucosidase I inhibitors.

  本发明描述了一组多羟基吲哚啉和喹哚啉及其酯类。这些化合物是从2,6-二脱氧-2,6-二脱氧-2,6-亚胺-1,3,4,5-四-O-(苯甲基)-D-甘露-L-戊醇或相应的N-取代化合物开始制备的。这些化合物在糖尿病治疗和作为α-葡萄糖苷酶I抑制剂方面是有用的。
• Synthesis of polyhydroxylated indolizidine and quinolizidine compounds--potent inhibitors of α-glucosidase I
  作者：Paul S. Liu、Roland S. Rogers、Mohinder S. Kang、Prasad S. Sunkara

  DOI：10.1016/s0040-4039(00)79409-3

  日期：1991.10

  Polyhydroxylated indolizidine 6a and quinolizidine 6b were synthesized from a common precursor, iminoheptitol 8. The target compounds are potent inhibitors of the glycoprotein trimming enzyme--alpha-glucosidase I.