(2R,3R)-2-Amino-hexane-1,3-diol | 50730-98-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3R)-2-Amino-hexane-1,3-diol
• 英文别名: (2R,3R)-2-aminohexane-1,3-diol
• CAS: 50730-98-8
• 化学式: C₆H₁₅NO₂
• 分子量: 133.191
• InChiKey: DNLRJWGHGZRUON-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2R,3R)-2-Amino-hexane-1,3-diol 在 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 生成 ((1R,2R)-2-Hydroxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Amino Acids and Peptides; 70.¹Optically Active α-Amino Acids,N-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acid from 2,3-Epoxy Alcohols

  摘要：

  2,3-环氧醇的三氯乙酰亚氨酯可分别转化为噁唑啉类化合物 5 和二氢噁嗪类化合物 6，具体取决于萃取物的结构和催化剂。五元环化合物 5 通过噁唑烷酮 11、12 和 13 转变成红δ-氨基δ-²-羟基酸（60-70% 来自环氧醇）。 δ-氨基酸和δ-取代的δ-氨基酸 10 以及相应的醛 9 可从二氢噁嗪 6 中获得（50-60% 来自环氧醇）。

  DOI：

  10.1055/s-1989-27216
• 作为产物：
  描述：

  [(2R,3R)-3-丙基-2-环氧乙烷基]甲醇 在 三氟化硼乙醚 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2R,3R)-2-Amino-hexane-1,3-diol
  参考文献：
  名称：

  Amino Acids and Peptides; 70.¹Optically Active α-Amino Acids,N-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acid from 2,3-Epoxy Alcohols

  摘要：

  2,3-环氧醇的三氯乙酰亚氨酯可分别转化为噁唑啉类化合物 5 和二氢噁嗪类化合物 6，具体取决于萃取物的结构和催化剂。五元环化合物 5 通过噁唑烷酮 11、12 和 13 转变成红δ-氨基δ-²-羟基酸（60-70% 来自环氧醇）。 δ-氨基酸和δ-取代的δ-氨基酸 10 以及相应的醛 9 可从二氢噁嗪 6 中获得（50-60% 来自环氧醇）。

  DOI：

  10.1055/s-1989-27216

文献信息

• Pharmaceutical formulations employing short-chain sphingolipids and their use
  申请人：Veldman J. Robert

  公开号：US20070082855A1

  公开（公告）日：2007-04-12

  This invention pertains to pharmaceutical formulations which comprise (i) a drug (e.g., an amphiphilic drug) (e.g., an anthracycline) (e.g., doxorubicin) and (ii) a short-chain sphingolipid (e.g., a short-chain glycosphingolipid or a short-chain sphingomyelin) (e.g., N-octanoyl-glucosylceramide, referred to as C 8 -GlcCer) (e.g., N-hexanoyl-sphingomyelin, referred to herein as C 6 -SM), and which provide improved drug delivery and efficacy. The short-chain sphingolipidis selected from compounds of the following formula: wherein: R 1 is independently: an O-linked saccharide group; or an O-linked polyhydric alcohol group; or: R 1 is independently: an O-linked (optionally N-(C 1-4 alkyl)-substituted amino)-C 1-6 alkyl-phosphate group; or an O-linked (polyhydric alcohol-substituted)-C 1-6 alkyl-phosphate group; R 2 is independently C 3-9 alkyl, and is independently unsubstituted or substituted; R 3 is independently C 7-19 alkyl, and is independently unsubstituted or substituted; R 4 is independently —H, —OH, or —O—C 1-4 alkyl; R N is independently —H or C 1-4 alkyl; the bond marked with an alpha (α) is independently a single bond or a double bond; if the bond marked with an alpha (α) is a double bond, then R 5 is —H; if the bond marked with an alpha (α) is a single bond, then R 5 is —H or —OH; the carbon atom marked (*) is independently in an R-configuration or an S-configuration; the carbon atom marked (**) is independently in an R-configuration or an S-configuration; and pharmaceutically acceptable salts, solvates, esters, ethers, chemically protected forms thereof. In one embodiment, the pharmaceutical formulation is a liposomal pharmaceutical formulation prepared using a mixture of lipids comprising, at least, vesicle-forming lipids (e.g., phospholipids) (e.g., phosphatidylcholines) (e.g., fully hydrogenated soy phosphatidylcholine (HSPC)) (e.g., dipalmitoyl-phosphatidylcholine (DPPC)) and said short-chain sphingolipid, and optionally cholesterol and optionally a vesicle-forming lipid which is derivatized with a polymer chain (e.g., a phosphatidylethanolamine (PE) which is derivatized with polyethyleneglycol (PEG)) (e.g., N-(carbonyl-methoxypolyethylene glycol 2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine sodium salt (MPEG2000-DSPE). The present invention also pertains to methods for the preparation and use of such formulations.
• Amino Acids and Peptides; 70.¹Optically Active α-Amino Acids,<i>N</i>-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acid from 2,3-Epoxy Alcohols
  作者：Ulrich Schmidt、Mathias Respondek、Albrecht Lieberknecht、Jürgen Werner、Peter Fischer

  DOI：10.1055/s-1989-27216

  日期：——

  Trichloroacetimidic esters of 2,3-epoxy alcohols are transformed into oxazolines 5 and dihydrooxazines 6, respectively, depending on the structure of the educts and the catalyst. The five-membered ring compounds 5 are transformed into erythro-α-amino-β-hydroxy acids (60-70% from epoxy alcohols) via oxazolidinones 11, 12, and 13. α-Amino acids and α-substituted α-amino acids 10 as well as the corresponding aldehydes 9 are obtained from the dihydrooxazines 6 (50-60% from epoxy alcohols).

  2,3-环氧醇的三氯乙酰亚氨酯可分别转化为噁唑啉类化合物 5 和二氢噁嗪类化合物 6，具体取决于萃取物的结构和催化剂。五元环化合物 5 通过噁唑烷酮 11、12 和 13 转变成红δ-氨基δ-²-羟基酸（60-70% 来自环氧醇）。 δ-氨基酸和δ-取代的δ-氨基酸 10 以及相应的醛 9 可从二氢噁嗪 6 中获得（50-60% 来自环氧醇）。