5-叠氮-5-脱氧-D-木酮糖 | 114395-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-叠氮-5-脱氧-D-木酮糖
• 英文名称: 5-Azido-5-desoxy-D-xylulose
• 英文别名: 5-azido-5-deoxy-D-xylulose；(3S,4R)-5-azido-1,3,4-trihydroxypentan-2-one
• CAS: 114395-15-2
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: ZCGGIPDFVSQUQO-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-叠氮-5-脱氧-D-木酮糖 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以74%的产率得到1,4-dideoxy-1,4-imino-D-arabitol
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00012a015
• 作为产物：
  描述：

  5-azido-5-deoxy-D-xylulose 1-phosphate 在 盐酸 作用下， 反应 24.0h， 生成 5-叠氮-5-脱氧-D-木酮糖
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00012a015

文献信息

• Process for the preparation of 2-hydroxymethyl-pyrolidine 3, 4-diols
  申请人：——

  公开号：US20040185539A1

  公开（公告）日：2004-09-23

  A process for the preparation of 2-hydroxymethyl-pyrrolidine-3,4-diols of the formulae comprising the steps of a) biooxidation of N-protected aminotetraols of the formula b) deprotection of the corresponding N-protected 5-amino-5-deoxy-pentulose c) hydrogenation of the corresponding 5-amino-5-deoxy-pentulose. 1

  一种制备式子中2-羟甲基吡咯烷-3,4-二醇的过程，包括以下步骤：a）对式子b中的N-保护氨基四醇进行生物氧化；b）对应的N-保护5-氨基-5-脱氧戊糖去保护；c）对应的5-氨基-5-脱氧戊糖进行氢化。1
• Process for the preparation of 2-hydroxymethyl-pyrrolidine-3,4-diols
  申请人：KAMPFEN Ulrich

  公开号：US20090155862A1

  公开（公告）日：2009-06-18

  A process for the preparation of 2-hydroxymethyl-pyrrolidine-3,4-diols of the formulae: including the steps of: a) bioxidation of N-protected aminotetraols of the formula: b) deprotection of the corresponding 5-amino-5-deoxy-pentulose of the formula: and c) hydrogenation of the corresponding 5-amino-5-deoxy-pentulose of the formula:

  一种制备式为2-羟甲基吡咯烷-3,4-二醇的过程，包括以下步骤： a) 对式为N-保护氨基四醇的生物氧化： b) 对应的5-氨基-5-脱氧戊糖的脱保护： c) 对应的5-氨基-5-脱氧戊糖的氢化：
• <scp>d</scp>-Fructose-6-Phosphate Aldolase-Catalyzed One-Pot Synthesis of Iminocyclitols
  作者：Masakazu Sugiyama、Zhangyong Hong、Pi-Hui Liang、Stephen M. Dean、Lisa J. Whalen、William A. Greenberg、Chi-Huey Wong

  DOI：10.1021/ja073911i

  日期：2007.11.28

  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.
• Ziegler, Thomas; Straub, Alexander; Effenberger, Franz, Angewandte Chemie, 1988, vol. 100, # 5, p. 737 - 738
  作者：Ziegler, Thomas、Straub, Alexander、Effenberger, Franz

  DOI：——

  日期：——
• ZIEGLER, THOMAS;STRAUB, ALEXANDER;EFFENBERGER, FRANZ, ANGEW. CHEM., 100,(1988) N, C. 737-738
  作者：ZIEGLER, THOMAS、STRAUB, ALEXANDER、EFFENBERGER, FRANZ

  DOI：——

  日期：——