(R)-3-[N-(苄氧羰基)氨基]-2-羟基丙醛 | 1000855-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-3-[N-(苄氧羰基)氨基]-2-羟基丙醛
• 英文名称: (R)-3-[N-(benzyloxycarbonyl)amino]-2-hydroxypropanal
• 英文别名: (R)-3-(N-benzyloxycarbonyl)amino-2-hydroxypropanal；((R)-2-hydroxy-3-oxo-propyl)-carbamic acid benzyl ester；benzyl N-[(2R)-2-hydroxy-3-oxopropyl]carbamate
• CAS: 1000855-32-2
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: DNYHWAFTTRLRTJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-[N-(苄氧羰基)氨基]-2-羟基丙醛 、 1-羟基-2-丁酮 在 fructose-6-phosphate aldolase sodium borate buffer 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 benzyl ((2R,3R,4S)-2,3,4-trihydroxy-5-oxoheptyl)carbamate
  参考文献：
  名称：

  d-Fructose-6-Phosphate Aldolase-Catalyzed One-Pot Synthesis of Iminocyclitols

  摘要：

  A one-pot chemoenzymatic method for the synthesis of a variety of new iminocyclitols from readily available, non-phosphorylated donor substrates has been developed. The method utilizes the recently discovered fructose-6-phosphate aldolase (FSA), which is functionally distinct from known aldolases in its tolerance of different donor substrates as well as acceptor substrates. Kinetic studies were performed with dihydroxyacetone (DHA), the presumed endogenous substrate for FSA, as well as hydroxy acetone (HA) and 1-hydroxy-2-butanone (HB) as donor substrates, in each case using glyceraidehyde-3-phosphate as acceptor substrate. Remarkably, FSA used the three donor substrates with equal efficiency, with k(cat)/K-M-values of 33, 75, and 20 M-1 s(-1), respectively. This level of donor substrate tolerance is unprecedented for an aldolase. Furthermore, DHA, HA, and HB were accepted as donors in FSA-catalyzed aldol reactions with a variety of azido- and Cbz-amino aldehyde acceptors. The broad substrate tolerance of FSA and the ability to circumvent the need for phosphorylated substrates allowed for one-pot synthesis of a number of known and novel iminocyclitols in good yields, and in a very concise fashion. New iminocyclitols were assayed as inhibitors against a panel of glycosidases. Compounds 15 and 16 were specific alpha-mannosidase inhibitors, and 24 and 26 were potent and selective inhibitors of beta-N-acetylglucosaminidases in the submicromolar range. Facile access to these compounds makes them attractive core structures for further inhibitor optimization.

  DOI：

  10.1021/ja073911i
• 作为产物：
  描述：

  (R)-3-(N-benzyloxycarbonyl)aminopropane-1,2-diol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (R)-3-[N-(苄氧羰基)氨基]-2-羟基丙醛
  参考文献：
  名称：

  有机合成中的D-果糖-6-磷酸醛缩酶：与糖有关的多羟基化合物的级联化学酶法制备

  摘要：

  D-果糖-6-磷酸醛缩酶（FSA）是具有已知治疗和研究兴趣或与药物开发相关的新颖结构的生物活性产品的替代合成构造的关键生物催化剂。提出了新颖的二羟基丙酮和羟丙酮与FSA催化的各种醛的醛醇加成反应（参见方案）。

  DOI：

  10.1002/chem.200802532

文献信息

• NOVEL HETEROCYCLYL COMPOUNDS
  申请人：Adam Jean-Michel

  公开号：US20100022518A1

  公开（公告）日：2010-01-28

  The invention is concerned with novel heterocyclyl compounds of formula (I): wherein A, X, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , m, n and p are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are antagonists of CCR2 receptor, CCR5 receptor and/or CCR3 receptor and may be used as medicaments.

  这项发明涉及式(I)的新异环烷基化合物：其中A、X、R3、R4、R5、R6、R7、R8、R9、R10、m、n和p如描述和索赔中所定义，并且其生理上可接受的盐。这些化合物是CCR2受体、CCR5受体和/或CCR3受体的拮抗剂，可用作药物。
• CHEMOENZYMATIC PROCESS FOR THE PREPARATION OF IMINOCYCLITOLS
  申请人：Consejo Superior de Investigaciones Cientificas (CSIC)

  公开号：EP2061892B1

  公开（公告）日：2010-02-03
• NOVEL HETEROCYCLYL COMPOUNDS FOR TREATMENT OF CARDIOVASCULAR DISEASE
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2307387A1

  公开（公告）日：2011-04-13
• DIAZEPAN AND PIPERAZINE DERIVATIVES MODULATORS OF CHEMOKINE RECEPTORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2321285A1

  公开（公告）日：2011-05-18
• Chemoenzymatic process for the preparation of iminocyclitols
  申请人：Clapés Saborit Pere

  公开号：US20100009417A1

  公开（公告）日：2010-01-14

  The present invention discloses a chemoenzymatic process for the preparation of an iminocyclitol corresponding to formula (I), (II), (III) or (IV), wherein: R 1 and R 2 are the same or different, and independently selected from the group consisting of: H, OH, hydroxymethyl, methyl, ethyl, butyl, pentyl, hexyl, octyl, isopropyl, isobutyl, 2-methylbutyl, and benzyl; R 3 is selected from the group consisting of: H, hydroxymethyl, hydroxyethyl, ethyl, butyl, pentyl, hexyl, octyl, dodecyl, isobutyl, isopropyl, isopentyl, 2-methylbutyl, benzyl, and phenylethyl; n: 0 or 1; the process comprising: (i) an aldol addition catalyzed by a D -fructose-6-phosphate aldolase enzyme (FSA) and an acceptor aminoaldehyde; and (ii) an intramolecular reductive amination of the addition adduct obtained in step (i) with H 2 , in the presence of a metallic catalyst, optionally being carried out said step (ii) in the presence of an aldehyde of formula R 3 —CHO, wherein R 3 is as defined above.