1,5-Didesoxy-1,5-imino-N-methyl-L-fucit | 117821-10-0

• 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: 1,5-Didesoxy-1,5-imino-N-methyl-L-fucit
• 英文别名: 1,5-dideoxy-1,5-imino-[N-methyl]-L-fucitol；N-Methyl-1,5-dideoxy-1,5-imino-L-fucitol；(2S,3R,4S,5R)-1,2-dimethylpiperidine-3,4,5-triol
• CAS: 117821-10-0
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: ARIAWFPKUVJPLU-WNJXEPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-甲基-3,4,5-哌啶三醇 在 钯 聚合甲醛 作用下， 以 甲醇 为溶剂， 生成 1,5-Didesoxy-1,5-imino-N-methyl-L-fucit
  参考文献：
  名称：

  Method of inhibiting virus

  摘要：

  一组含有环中氮原子并且环上有2到3个羟基取代基的五元和六元杂环化合物是人类免疫缺陷病毒的有效抑制剂。

  公开号：

  US04999360A1

文献信息

• Heterocyclic compounds for inhibiting virus
  申请人：Monsanto Company

  公开号：EP0322395A1

  公开（公告）日：1989-06-28

  Various heterocyclic compounds, namely (a) the N-methyl derivative of di(hydroxymethyl)-dihydroxy­pyrrolidine, (b) 1,4-dideoxy-1,4-imino-L-arabinitol, (c) 1,4-dideoxy-1,4-imino-L-ribitol, (d) 1,4-dideoxy-1,4-imino-D-ribitol, (e) 1,4-dideoxy-1,4-imino-(N-methyl)-L-arabinitol, (f) 1,4-dideoxy-1,4-imino-(N-methyl)-D-ribitol, (g) 1,4-dideoxy-1,4-benzylimino-L-ribitol, (h) 1,4-dideoxy-1,4-imino-D-talitol, (i) the N-methyl derivative of deoxymannojirimycin, (j) 1,5-dideoxy-1,5-imino-L-fuconolactam, (k) 1,5-dideoxy-1,5-imino-(N-methyl)-L-fucitol, (l) 1,5-dideoxy-1,5-imino-(N-ω-methyl caproate)-L-fucitol, and their pharmaceutically acceptable salt derivatives are useful as inhibiting agents of human immunodeficiency virus. Compounds (a), (e), (j), (k) and (l) are new.

  各种杂环化合物，即 (a) 二（羟甲基）-二羟基吡咯烷的 N-甲基衍生物、 (b) 1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇、 (c) 1,4-二脱氧-1,4-亚氨基-L-核糖醇、 (d) 1,4-二脱氧-1,4-亚氨基-D-核糖醇、 (e) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-L-阿拉伯糖醇、 (f) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-D-核糖醇、 (g) 1,4-二脱氧-1,4-苄基亚氨基-L-核糖醇、 (h) 1,4-二脱氧-1,4-亚氨基-D-谷糖醇、 (i) 脱氧曼尻霉素的 N-甲基衍生物、 (j) 1,5-二脱氧-1,5-亚氨基-L-岩藻内酰胺、 (k) 1,5-二脱氧-1,5-亚氨基-(N-甲基)-L-岩藻糖醇、 (l) 1,5-二脱氧-1,5-亚氨基-(N-ω-甲基己酸酯)-L-岩藻糖醇、 及其药学上可接受的盐衍生物可用作人类免疫缺陷病毒的抑制剂。化合物(a)、(e)、(j)、(k)和(l)是新化合物。
• Paulsen, Hans; Matzke, Michael; Orthen, Bruno, Liebigs Annalen der Chemie, 1990, # 10, p. 953 - 963
  作者：Paulsen, Hans、Matzke, Michael、Orthen, Bruno、Nuck, Rolf、Reutter, Werner

  DOI：——

  日期：——
• Glycosidase Inhibitors:  Synthesis of Enantiomerically Pure Aza-Sugars from Schiff Base Amino Esters via Tandem Reduction-Alkenylation and Osmylation
  作者：Robin Polt、Dalibor Sames、Jason Chruma

  DOI：10.1021/jo9820115

  日期：1999.8.1

  Nitrogen-in-the-ring "aza-sugars" have been synthesized in enantiomerically pure form from the amino acid L-alanine in excellent overall yield. The O'Donnell's Schiff base of L-alanine methyl ester 9a was converted to ate-sugar L-fuco-1-deoxy-nojirimycin, 18, and to the epimer L-gulo-1-deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl- and benzyl-protected (E)-3-lithio-2-propen-1-ols, and the use of these alkenyllithiums with iBu(5)Al(2)H as nucleophiles in the three-selective tandem reduction-alkenylation of the Schiff base esters is described. Osmium-catalyzed cis-oxygenation of the resulting olefin products was selective for the galacto (fuco) amino polyols in all cases for the acyclic olefins, and was gulo-selective for the cyclic D-4,5-dihydropyridine pivalate, 17c. TEMPO-NaOCl was selective for oxidation of the primary position of the acyclic Schiff bases, and allowed for minimal protection/deprotection of the intermediates. The resulting N-benzhydryl heterocycles were easily deprotected with H-2-Pd at atmospheric pressure.
• PAULSEN, HANS;MATZKE, MICHAEL;ORTHEN, BRUNO;NUCK, ROLF;REUTTER, WERNER, LIEBIGS ANN. CHEM.,(1990) N0, C. 953-963
  作者：PAULSEN, HANS、MATZKE, MICHAEL、ORTHEN, BRUNO、NUCK, ROLF、REUTTER, WERNER

  DOI：——

  日期：——
• US5043416A
  申请人：——

  公开号：US5043416A

  公开（公告）日：1991-08-27