methyl-3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-β-D-ribohexapyranoside | 4338-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-β-D-ribohexapyranoside
• 英文别名: methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-β-D-glucopyranoside；methyl-(tri-O-acetyl-3-acetylamino-3-deoxy-β-D-glucopyranoside)；Methyl-(tri-O-acetyl-3-acetylamino-3-desoxy-β-D-glucopyranosid)；Methyl-3-acetamido-3-deoxy-2,4,6-tri-O-acetyl-β-D-glucosid；Methyl-3-acetamido-3-deoxy-β-D-glucosid-2,4,6-triacetat；[(2R,3S,4S,5R,6R)-4-acetamido-3,5-diacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 4338-42-5
• 化学式: C₁₅H₂₃NO₉
• 分子量: 361.349
• InChiKey: URHNGESEFHBZNP-XLWJZTARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl-3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-β-D-ribohexapyranoside 在 chromium(VI) oxide 、 乙酸酐 、 溶剂黄146 作用下， 反应 2.0h， 以85%的产率得到methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-D-xylo-hex-5-ulosonate
  参考文献：
  名称：

  A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

  摘要：

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.016
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium acetate 、 乙酸酐 作用下， 生成 methyl-3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-β-D-ribohexapyranoside
  参考文献：
  名称：

  334.脱水甲基己糖化物对碱性试剂的行为。3-氨基葡萄糖和2-氨基葡萄糖的衍生物的制备

  摘要：

  DOI：

  10.1039/jr9380001810

文献信息

• [EN] SELECTIVE OXIDATION OF CARBOHYDRATES<br/>[FR] OXYDATION SÉLECTIVE DES GLUCIDES
  申请人：UNIV GRONINGEN

  公开号：WO2013191549A1

  公开（公告）日：2013-12-27

  The invention relates to the field of carbohydrate chemistry. Provided is a process for the regioselective oxidation of a single secondary hydroxy function of a carbohydrate substrate comprising two or more secondary hydroxy functions, comprising contacting the carbohydrate substrate in a solvent in the presence of a transition metal catalyst complex with an oxidizing agent to yield a mono-oxidized carbohydrate.

  该发明涉及碳水化合物化学领域。提供了一种用于对碳水化合物底物中的单个次生羟基功能进行区域选择氧化的方法，该底物包含两个或更多个次生羟基功能，包括将碳水化合物底物在溶剂中与过渡金属催化剂复合物和氧化剂接触以产生单氧化的碳水化合物。
• Regio- and stereo-selective transformation of glycosides to amino-glycosides. Practical synthesis of amino-sugars, 4-amino-4-deoxy-D-galactose, 4-amino-4-deoxy-L-arabinose, 3-amino-3-deoxy-D-allose, 3-amino-3-deoxy-D-glucose, 3-amino-3-deoxy-D-ribose, 3-amino-3-deoxy-D-xylose, 2-amino-2-deoxy-D-mannose, and 5-amino-5-deoxy-D-glucose (nojirimycin).
  作者：Yoshisuke TSUDA、Yukihiro OKUNO、Minoru IWAKI、Kimihiro KANEMITSU

  DOI：10.1248/cpb.37.2673

  日期：——

  One of the hydroxyl groups in glycosides was regio- and stereo-selectively converted to an amino group as follows. A glycoside was regioselectively converted to an oxo-glycoside by bis-tributyltin oxide-bromine oxidation. Oximation of this and reduction of the resulting oxime in a stereoselective manner gave an amino-glycoside in a satisfactory yield.By application of this method, 4-amino-4-deoxy-D-galactose, 4-amino-4-deoxy-L-arabinose, 3-amino-3-deoxy-D-allose, 3-amino-3-deoxy-D-glucose, 3-amino-3-deoxy-D-ribose, 3-amino-3-deoxy-D-xylose, and 2-amino-2-deoxy-D-mannose were synthesized in satisfactory yields from D-xylose or D-glucose as their α- or β-methyl glycosides. The method also provided a practical synthetic route to nojirimycin (5-amino-5-deoxy-D-glucose), a glucosidase-inhibitory antibiotic, from D-glucose.

  苷中的一个羟基可通过以下方法进行区域和立体选择性地转化为氨基。通过双三丁基氧化锡-溴氧化作用，苷可以选择性地转化为氧化苷。以立体选择性的方式将其氧化并还原生成的肟，即可得到产率令人满意的氨基糖苷。应用这种方法，以 D-木糖或 D-葡萄糖为α-或β-甲基糖苷，合成了 4-氨基-4-脱氧-D-半乳糖、4-氨基-4-脱氧-L-阿拉伯糖、3-氨基-3-脱氧-D-阿洛糖、3-氨基-3-脱氧-D-葡萄糖、3-氨基-3-脱氧-D-核糖、3-氨基-3-脱氧-D-木糖和 2-氨基-2-脱氧-D-甘露糖，产率令人满意。该方法还提供了一条从 D-葡萄糖中合成诺吉霉素（5-氨基-5-脱氧-D-葡萄糖）的实用途径，诺吉霉素是一种葡萄糖苷酶抑制抗生素。
• 334. The behaviour of anhydromethylhexosides towards alkaline reagents. Preparation of derivatives of 3-amino-glucose and 2-amino-altrose
  作者：S. Peat、L. F. Wiggins

  DOI：10.1039/jr9380001810

  日期：——
• TSUDA, YOSHISUKE;OKUNO, YUKIHIRO;IWAKI, MINORU;KANEMITSU, KIMIHIRO, CHEM. AND PHARM. BULL., 37,(1989) N0, C. 2673-2678
  作者：TSUDA, YOSHISUKE、OKUNO, YUKIHIRO、IWAKI, MINORU、KANEMITSU, KIMIHIRO

  DOI：——

  日期：——
• A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol
  作者：Ondřej Šimák、Jan Staněk、Jitka Moravcová

  DOI：10.1016/j.carres.2009.03.016

  日期：2009.5

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.