methyl (3aS,5R,9aR,9bR)-2,2-dimethyl-7-oxohexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridine-5-carboxylate | 1416449-44-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3aS,5R,9aR,9bR)-2,2-dimethyl-7-oxohexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridine-5-carboxylate
• 英文别名: methyl (1R,2R,6S,8R)-4,4-dimethyl-10-oxo-3,5,11-trioxa-9-azatricyclo[7.3.0.02,6]dodecane-8-carboxylate
• CAS: 1416449-44-9
• 化学式: C₁₂H₁₇NO₆
• 分子量: 271.27
• InChiKey: MTGYSSSXYOPCHM-LURQLKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3aS,5R,9aR,9bR)-2,2-dimethyl-7-oxohexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridine-5-carboxylate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (2R,3R,4S,6R)-3,4-dihydroxy-2,6-bis(hydroxymethyl)-1-methylpiperidinium chloride
  参考文献：
  名称：

  Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (S)-Vinylglycinol

  摘要：

  An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the alpha-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.

  DOI：

  10.1021/ol303213r
• 作为产物：
  描述：

  (4S)-3-[(1R)-1-tributylstannylbut-3-en-1-yl]-4-ethenyl-1,3-oxazolidin-2-one 在 Grubbs catalyst first generation 、 四氧化锇 、 正丁基锂 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 12.33h， 生成 methyl (3aS,5R,9aR,9bR)-2,2-dimethyl-7-oxohexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]pyridine-5-carboxylate
  参考文献：
  名称：

  Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (S)-Vinylglycinol

  摘要：

  An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the alpha-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.

  DOI：

  10.1021/ol303213r

文献信息

• A versatile stereocontrolled synthesis of 2-deoxyiminosugar <i>C</i>-glycosides and their evaluation as glycosidase inhibitors
  作者：Alexandre Lumbroso、Clément Berthonneau、Isabelle Beaudet、Jean-Paul Quintard、Aurélien Planchat、M. Isabel García-Moreno、Carmen Ortiz Mellet、Erwan Le Grognec

  DOI：10.1039/d0ob02249g

  日期：——

  iminosugar hydrochlorides. A primary evaluation of the designed iminosugar C-glycosides as glycosidase inhibitors suggests candidates for the selective inhibition of α-galactosidase, amyloglycosidase and naringinase. Beyond the reported results, the method constitutes a highly modulable route for the synthesis of well stereodefined iminosugar C-glycosides, an advantage which might be used for the design

  （R，S）或（S，S）-2，6-二取代的脱氢哌啶的高对映选择性合成先前已经通过相应的甲锡烷基化的脱氢哌啶或其前体的Sn / Li重金属化而实现。在此，我们先后考虑他们的普强公司的SYN二羟基化的抗二羟基化通过环氧化反应，随后环氧化物开环反应。首先报道了这些反应的立体化学过程，包括使用适当的保护基，然后考虑将所得化合物转化为NH或NMe亚氨基糖盐酸盐。设计的亚氨基糖的初步评估作为糖苷酶抑制剂的C-糖苷暗示了α-半乳糖苷酶，淀粉糖苷酶和柚皮苷酶的选择性抑制候选物。除了所报道的结果之外，该方法还构成了高度可调节的路线，用于合成立体明确的亚氨基糖C-糖苷，该优点可用于设计亚氨基糖以增强其生物学特性。
• Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (<i>S</i>)-Vinylglycinol
  作者：Alexandre Lumbroso、Isabelle Beaudet、Loïc Toupet、Erwan Le Grognec、Jean-Paul Quintard

  DOI：10.1021/ol303213r

  日期：2013.1.4

  An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the alpha-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.