4-amino-4-deoxy-5,6-O-isopropylidene-7-O-methanesulfonyl-2,3,8-tri-O-tert-butyldimethylsilyl-L-threo-L-altro-octono-1,4-lactam | 874350-65-9

• 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-5,6-O-isopropylidene-7-O-methanesulfonyl-2,3,8-tri-O-tert-butyldimethylsilyl-L-threo-L-altro-octono-1,4-lactam
• 英文别名: 5,6-O-isopropylidene-7-O-methanesulphonyl-2,3,8-tri-O-tert-butyldimethylsilyl-L-threo-L-altro-octono-γ-lactam；[(1S)-1-[(4S,5R)-5-[(2S,3S,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-oxopyrrolidin-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] methanesulfonate
• CAS: 874350-65-9
• 化学式: C₃₀H₆₃NO₉SSi₃
• 分子量: 698.154
• InChiKey: SQCKSJHJFPFFLU-JXQUOSBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-4-deoxy-5,6-O-isopropylidene-7-O-methanesulfonyl-2,3,8-tri-O-tert-butyldimethylsilyl-L-threo-L-altro-octono-1,4-lactam 在 硼烷四氢呋喃络合物 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 生成 casuarine
  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：

  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 、 三乙胺 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 7.0h， 生成 4-amino-4-deoxy-5,6-O-isopropylidene-7-O-methanesulfonyl-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

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.