(-)-2-<2-Hydroxy-ethoxy>-butan-1,4-diol | 68733-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-2-<2-Hydroxy-ethoxy>-butan-1,4-diol
• 英文别名: <3-Hydroxy-1-hydroxymethyl-propyl>-<2-hydroxy-ethyl>-aether；(S)-2-(2-hydroxy-ethoxy)-butane-1,4-diol；(2S)-2-(2-hydroxyethoxy)butane-1,4-diol
• CAS: 68733-01-7
• 化学式: C₆H₁₄O₄
• 分子量: 150.175
• InChiKey: IUSXXZSVVJZZJS-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-Anhydro-4-deoxy-D-lyxo-hexit 生成 (-)-2-<2-Hydroxy-ethoxy>-butan-1,4-diol
  参考文献：
  名称：

  THE REACTION OF UNSATURATED CARBOHYDRATES WITH CARBON MONOXIDE AND HYDROGEN: III. STRUCTURE AND STEREOCHEMISTRY OF THE HEXITOLS FROM 3,4-DI-O-ACETYL-D-ARABINAL

  摘要：

  不详

  DOI：

  10.1139/v64-297

文献信息

• Method of manufacturing ruboxistarin
  申请人：Zentiva, k.s.

  公开号：EP2181999A1

  公开（公告）日：2010-05-05

  Method of manufacturing ruboxistaurin, comprising the steps of preparation of L-2-deoxyribose 1-cyano-3,4-dibenzoate, followed by deprotection to 1-cyano L-2-deoxyribose, oxidative cleaving to (S)-4-hydroxy-2-(2-hydroxy-ethoxy)-butyronitrile and transformation to the methanesulfonic acid (S)-3-cyano-3-(2-methanesulfonyloxyethoxy)-propyl ester, then coupling with 1-substituted-3,4-bis(3-indolyl)maleimide leading to 9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13] oxadiazacyclohexadecine-18,20(19H)-dione, 6,7,10,11-tetrahydro-19-substituted-9(S)-cyano, followed by methylation of the amino group and deprotection forming 5,21:12,17-dimetheno-9H-dibenzo[e,k]furo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20-dione, 6,7,10,11-tetrahydro-9-[(dimethylamino)methyl]-, (S)- (9CI), and the final step consisting of imido preparation to form ruboxistaurin.

  生产鲁博西他林的方法，包括以下步骤：制备L-2-去氧核糖-1-氰-3,4-二苯甲酸酯，然后去保护成为1-氰基L-2-去氧核糖，氧化断裂成(S)-4-羟基-2-(2-羟基乙氧基)-丁腈，并转化为甲磺酸(S)-3-氰基-3-(2-甲磺酰氧乙氧基)-丙基酯，然后与1-取代-3,4-双(3-吲哚基)马来酰亚胺偶联，得到9H,18H-5,21:12,17-二甲烯二苯并[e,k]吡咯并[3,4-h][1,4,13]噁二氮杂环十六烷-18,20(19H)-二酮，6,7,10,11-四氢-19-取代-9(S)-氰基，然后甲基化氨基团并去保护，形成5,21:12,17-二甲烯-9H-二苯并[e,k]呋喃[3,4-h][1,4,13]噁二氮杂环十六烷-18,20-二酮，6,7,10,11-四氢-9-[(二甲氨基)甲基]-，(S)- (9CI)，最后一步是制备亚砜以形成鲁博西他林。
• THE REACTION OF UNSATURATED CARBOHYDRATES WITH CARBON MONOXIDE AND HYDROGEN: II. STRUCTURE AND STEREOCHEMISTRY OF THE ANHYDRODEOXYHEXITOLS FROM 3,4-DI-<i>O</i>-ACETYL-<scp>D</scp>-XYLAL
  作者：Alex Rosenthal、Derek Abson

  DOI：10.1139/v64-272

  日期：1964.8.1

  3,4-Di-O-acetyl-D-xylal reacted with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl to yield 1,5-anhydro-4-deoxy-D-arabino-hexitol (I) and 1,5-anhydro-4-deoxy-L-xylo-hexitol (II). The stereochemistry at C-5 of the hexitols was elucidated by correlation with the triol ether (VI) obtained by sodium borohydride reduction of the periodate oxidation product of 1,4-anhydro-5-deoxy-D-arabino-hexitol

  3,4-Di-O-乙酰基-D-二甲苯在八羰基二钴存在下与一氧化碳和氢气反应，生成 1,5-脱水-4-脱氧-D-阿拉伯-己糖醇 (I) 和 1,5- anhydro-4-deoxy-L-xylo-hexitol (II)。通过与通过硼氢化钠还原 1,4-脱水-5-脱氧-D-阿拉伯-己糖醇 (VII) 的高碘酸盐氧化产物获得的三醇醚 (VI) 的相关性，阐明了己糖醇的 C-5 立体化学。3,4-二-O-乙酰基-D-二甲苯醛与一氧化碳和氘反应得到1,5-脱水-4-脱氧-D-阿拉伯-己糖醇-4,6,6-H32 (VIII)和1， 5-anhydro-4-deoxy-L-xylo-hexitol-4,6,6-H32 (IX)。对正常和氘化脱水脱氧己糖醇的核磁共振 (nmr) 光谱的检查证实了结构分配，并表明双键发生顺式加成得到 (IX)。