4-amino-4-deoxy-2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-erythro-L-altro-octono-1,4-lactam | 874350-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-4-deoxy-2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-erythro-L-altro-octono-1,4-lactam
• 英文别名: 5,6-O-isopropylidene-2,3-di-O-tert-butyldimethylsilyl-D-erythro-L-altro-octono-γ-lactam；(3R,4S,5S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidin-2-one
• CAS: 874350-59-1
• 化学式: C₂₃H₄₇NO₇Si₂
• 分子量: 505.8
• InChiKey: HCCIRHMRASNQGT-MJJLTSLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-4-deoxy-2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-erythro-L-altro-octono-1,4-lactam 在 吡啶 、 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 5.0h， 生成 4-amino-4-deoxy-5,6-O-isopropylidene-2,3,8-tri-O-tert-butyldimethylsilyl-L-threo-L-altro-octono-1,4-lactam
  参考文献：
  名称：

  Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

  摘要：

  3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from D-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomcsylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.005
• 作为产物：
  描述：

  (R)-4-Azido-2,3-dihydroxy-4-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-butyric acid methyl ester 在 palladium hydroxide - carbon 咪唑 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 56.0h， 生成 4-amino-4-deoxy-2,3-di-O-tert-butyldimethylsilyl-5,6-O-isopropylidene-D-erythro-L-altro-octono-1,4-lactam
  参考文献：
  名称：

  Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

  摘要：

  3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from D-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomcsylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.005

文献信息

• [EN] SYNTHESIS OF POLYHYDROXYLATED ALKALOIDS<br/>[FR] SYNTHÈSE DES ALCALOÏDES POLYHYDROXYLÉS
  申请人：MNL PHARMA LTD

  公开号：WO2006008493A1

  公开（公告）日：2006-01-26

  A process for the production of a polyhydroxylated bicyclic (e.g. pyrrolizidine such as casuarine (10), indolizidine or quinolizidine) alkaloid comprises the cyclisation of a pyrrolidine or piperidine intermediate having three or more free hydroxyl groups.

  一种用于生产多羟基双环（例如吡咯里西啶，例如相思豆碱（10）、吲哚里西啶或喹诺里西啶）生物碱的过程，包括将具有三个或更多自由羟基的吡咯烷或哌啶中间体进行环合。
• Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine
  作者：Jeroen Van Ameijde、Graeme Horne、Mark R. Wormald、Raymond A. Dwek、Robert J. Nash、Paul Wyn Jones、Emma L. Evinson、George W.J. Fleet

  DOI：10.1016/j.tetasy.2006.10.005

  日期：2006.10

  3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from D-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomcsylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported. (c) 2006 Elsevier Ltd. All rights reserved.