N-Methyl-5-amino-5-deoxy-2,3-isopropylidene-4-O-methyl-D-ribono-1,5-lactam | 208982-95-0

• 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: N-Methyl-5-amino-5-deoxy-2,3-isopropylidene-4-O-methyl-D-ribono-1,5-lactam
• 英文别名: (3aR,7R,7aR)-7-methoxy-2,2,5-trimethyl-3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one
• CAS: 208982-95-0
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: YURKRDZEUNACGT-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-Methyl-5-amino-5-deoxy-2,3-isopropylidene-4-O-methyl-D-ribono-1,5-lactam 、 alkaline earth salt of/the/ methylsulfuric acid 在 三甲基氯硅烷 作用下， 生成 Methyl 2,6-dideoxy-3,4-O-isopropylidene-5-O-methyl-2,6-(methylimino)-D-allonate
  参考文献：
  名称：

  Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation

  摘要：

  The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)(5) and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)(5)-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is p-selective and has been applied further to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<691::aid-chem691>3.0.co;2-e
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 、 碘甲烷 在 吡啶 、 sodium azide 、 氢气 、 sodium hydride 、 对甲苯磺酰氯 作用下， 生成 N-Methyl-5-amino-5-deoxy-2,3-isopropylidene-4-O-methyl-D-ribono-1,5-lactam
  参考文献：
  名称：

  Diastereoselective synthesis of 2,6-Imino-D-allonates from chromium carbene iminosugars

  摘要：

  Nucleophilic addition of methanol to ketene equivalents generated by photolysis of pentacarbonyl[1,5-imino-D-ribopyranosylidene]chromium complexes leads diastereospecifically to D-allonates. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00620-0

文献信息

• Diastereoselective synthesis of 2,6-Imino-D-allonates from chromium carbene iminosugars
  作者：Markus Klumpe、Karl Heinz Dötz

  DOI：10.1016/s0040-4039(98)00620-0

  日期：1998.5

  Nucleophilic addition of methanol to ketene equivalents generated by photolysis of pentacarbonyl[1,5-imino-D-ribopyranosylidene]chromium complexes leads diastereospecifically to D-allonates. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation
  作者：Karl Heinz Dötz、Markus Klumpe、Martin Nieger

  DOI：10.1002/(sici)1521-3765(19990201)5:2<691::aid-chem691>3.0.co;2-e

  日期：1999.2.1

  The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)(5) and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)(5)-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is p-selective and has been applied further to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate.