N-formyl-1-amino-1-deoxy-L-xylitol | 132803-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-formyl-1-amino-1-deoxy-L-xylitol
• 英文别名: N-[(2R,3S,4S)-2,3,4,5-tetrahydroxypentyl]formamide
• CAS: 132803-80-6
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: TTZBGONHUFMKGZ-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-formyl-1-amino-1-deoxy-L-xylitol 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以47%的产率得到1-amino-1-deoxy-L-xylitol
  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：

  N-[(2R,3S)-2,3,5-trihydroxy-4-oxo-pentyl]formamide 在 sodium formate 、 NADH 作用下， 以 水 为溶剂， 反应 48.0h， 以54%的产率得到N-formyl-1-amino-1-deoxy-L-xylitol
  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-PYROLIDINE-3,4-DIOLS
  申请人：Lonza AG

  公开号：EP1379676A2

  公开（公告）日：2004-01-14
• [EN] PROCESS FOR THE PREPARATION OF 2-HYDROXYMETHYL-PYROLIDINE-3,4-DIOLS<br/>[FR] PROCEDE DE PREPARATION DE 2-HYDROXYMETHYL-PYROLIDINE-3,4-DIOLS
  申请人：LONZA AG

  公开号：WO2002074737A2

  公开（公告）日：2002-09-26

  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.
• .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.