(2S)-3-azido-1,1-diethoxypropan-2-ol | 128572-84-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S)-3-azido-1,1-diethoxypropan-2-ol
• CAS: 128572-84-9
• 化学式: C₇H₁₅N₃O₃
• 分子量: 189.214
• InChiKey: PVICMFYQTFWJGQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-3-azido-1,1-diethoxypropan-2-ol 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以40%的产率得到(R)-2-(diethoxymethyl)aziridine
  参考文献：
  名称：

  Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors

  摘要：

  A combined fructose 1,6-diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6-deoxyazasugars were prepared by direct hydrogenolysis of the aldolase product without removal of the 6-phosphate group. Both (R)- and (S)-3-azido-2-acetamidopropanal used as substrates in the aldolase reactions were prepared from the corresponding lipase-resolved 2-hydroxy species followed by formation of an aziridine intermediate and opening of the aziridine with azide. Evaluation of these azasugars and their diastereomerically pure tertiary amine oxides as well as 5-thioglucose and its sulfoxide derivatives as glycosidase inhibitors was carried out. It was found that all synthetic azasugars and 5-thioglucose were strong inhibitors, but oxidation of the ring heteroatom weakened the inhibition. With the aid of molecular modeling and inhibition analysis, a structure-K(i) relation of inhibitors was established which provides useful information for the design of new glycosidase inhibitors.

  DOI：

  10.1021/ja00016a039
• 作为产物：
  描述：

  (D,L)-3-azido-2-hydroxypropanal diethyl acetal 在 吡啶 、 甲醇 、 sodium hydride 作用下， 反应 2.0h， 生成 (2S)-3-azido-1,1-diethoxypropan-2-ol
  参考文献：
  名称：

  Pederson, Richard L.; Wong, Chi-Huey, Heterocycles, 1989, vol. 28, # 1, p. 477 - 480

  摘要：

  DOI：

文献信息

• Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions: preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, 1,4-dideoxy-1,4-imino-D-arabinitol, and fagomine
  作者：Claus H. Von der Osten、Anthony J. Sinskey、Carlos F. Barbas、Richard L. Pederson、Yi Fong Wang、Chi Huey Wong

  DOI：10.1021/ja00193a025

  日期：1989.5

  60 days while that of the rabbit enzyme is 2 days (Figure 1 ) . To illustrate the use of the microbial enzyme in preparative-scale synthesis, the polyhydroxylated alkaloids 1J-dideoxy1,5-iminoD-glUCitOl (1 -deoxynojirimycin, 5), 1,5-dideoxy-l,5-imino-~'Massachusetts Institute of Technology. *Texas A&M University. 0002-7863/89/1511-3924$01.50/0 mannitol (1 -deoxymannojirimycin, 6 ) , 1,4-dideoxy1,4-imino-Darabinitol

  酶促醛醇缩合和催化分子内还原胺化的组合已用于多羟基生物碱的高产不对称合成，包括 1-脱氧野尻霉素、1-脱氧甘露野尻霉素、1,4-二脱氧 1,4-亚氨基-~-阿拉伯糖醇和 fagomine。在大肠杆菌中过表达的含有 Znzt 的大肠杆菌果糖 1,6-二磷酸醛缩酶用于合成。该酶在含有 0.3 mM ZnCl 的水溶液中具有出色的稳定性，半衰期为 60 天，而兔肌肉中的酶为 2 天。反应在没有官能团保护的温和条件下进行。磷酸二羟基丙酮或二羟基丙酮与无机砷酸盐的混合物均可用作羟醛反应中的供体。醛醇受体 (R) 和 (S)-3-叠氮基-2-羟基丙醛是通过脂肪酶催化拆分外消旋缩醛前体制备的。最近的研究证明了醛缩酶催化的合成效用 在自然界中发现的超过 15 种醛缩酶中，最常使用的是来自兔肌肉的无金属席夫碱形成果糖 1,6-二磷酸 (FDP) 醛缩酶。对磷酸二羟基丙酮 (Ia) 具有高度特异性，但接受多种醛作为第二底物。供体
• PEDERSON, RICHARD L.;LIU, KEVIN K. -C.;RUTAN, JAMES F.;CHEN, LIHREN;WONG,+, J. ORG. CHEM., 55,(1990) N6, C. 4897-4901
  作者：PEDERSON, RICHARD L.、LIU, KEVIN K. -C.、RUTAN, JAMES F.、CHEN, LIHREN、WONG,+

  DOI：——

  日期：——