[(2R,3S,4R,5S)-5-azido-2,3,4-trihydroxyoxan-2-yl]methyl dihydrogen phosphate | 136616-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: [(2R,3S,4R,5S)-5-azido-2,3,4-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 136616-71-2
• 化学式: C₆H₁₂N₃O₈P
• 分子量: 285.15
• InChiKey: QVHSQFWFOUGOPC-BGPJRJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5S)-5-azido-2,3,4-trihydroxyoxan-2-yl]methyl dihydrogen phosphate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 acid phosphatase 、 sodium acetate buffer 、 氢气 、 sodium cyanoborohydride 作用下， 反应 72.25h， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  Facile approach towards phosphorylated azasugars as potential glycosyl phosphate mimics

  摘要：

  A sequence of two chemoselective reductions enables the stereoselective synthesis of phosphorylated azasugars starting from products of dihydroxyacetonephosphate-dependent aldolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00322-5
• 作为产物：
  描述：

  1-羟基-3-(磷酰氧基)-2-丙酮 、 2-azido-3-hydroxy-propionaldehyde 在 rabbit muscle aldolase 作用下， 以54%的产率得到[(2R,3S,4R,5S)-5-azido-2,3,4-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Facile approach towards phosphorylated azasugars as potential glycosyl phosphate mimics

  摘要：

  A sequence of two chemoselective reductions enables the stereoselective synthesis of phosphorylated azasugars starting from products of dihydroxyacetonephosphate-dependent aldolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00322-5

文献信息

• .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  作者：Rebecca R. Hung、Julie Ann Straub、George M. Whitesides

  DOI：10.1021/jo00012a015

  日期：1991.6

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.
• Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars
  作者：Kevin K. C. Liu、Tetsuya Kajimoto、Lihren Chen、Ziyang Zhong、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/jo00022a013

  日期：1991.10

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.
• HUNG, REBECCA R.;STRAUB, JULIE ANN;WHITESIDES, GEORGE M., J. ORG. CHEM., 56,(1991) N2, C. 3849-3855
  作者：HUNG, REBECCA R.、STRAUB, JULIE ANN、WHITESIDES, GEORGE M.

  DOI：——

  日期：——
• Facile approach towards phosphorylated azasugars as potential glycosyl phosphate mimics
  作者：Matthias Schuster、Siegfried Blechert

  DOI：10.1016/s0957-4166(99)00322-5

  日期：1999.8

  A sequence of two chemoselective reductions enables the stereoselective synthesis of phosphorylated azasugars starting from products of dihydroxyacetonephosphate-dependent aldolases. (C) 1999 Elsevier Science Ltd. All rights reserved.