2,3,4,6-tetra-O-benzyl-D-galactonamide | 158349-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-D-galactonamide
• 英文别名: (2R,3S,4S,5R)-5-hydroxy-2,3,4,6-tetrakis(phenylmethoxy)hexanamide
• CAS: 158349-18-9
• 化学式: C₃₄H₃₇NO₆
• 分子量: 555.671
• InChiKey: QSTAZHHZHIPWRR-JDIHBLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactonamide 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 2-O-octyl-3,5-dihydroxy-6-methylpyridine
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 potassium tert-butylate 、 氨 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.08h， 生成 2,3,4,6-tetra-O-benzyl-D-galactonamide
  参考文献：
  名称：

  An unusual synthesis of 2-pyridone and 3,5-dihydroxypyridine from a carbohydrate

  摘要：

  An unusual aromatization to perbenzylated 3,5-dihydroxy-6-(hydroxymethyl)-2-pyridone was demonstrated utilizing sugar lactam, under strong basic conditions, derived from D-Galactose. 2-Pyridone was efficiently converted into a pharmaceutically relevant structure 3,5-dihydroxy pyridine salt to demonstrate its synthetic utility. This result is the first report for 2-pyridone synthesis from a carbohydrate, and also first of its kind for a novel 3,5-dihydroxypyridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.083

文献信息

• Glycosylidene Carbenes. Part 32
  作者：Sissi E. Mangholz、Karin Briner、Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.200390202

  日期：2003.7

  Acylation and sulfonylation of the N,N′-unsubstituted glucosylidenespirodiaziridines 1A/1B 95 : 5 with Ac2O, BzCl, FmocCl, TsCl, (naphthalen-2-yl)sulfonyl, and (2,4,6-triisopropylphenyl)sulfonyl chloride, and concomitant rearrangement gave the acylated and sulfonylated gluconolactone hydrazones 2B–2G in 40–83% yield (Scheme 2). Similarly, the galacto and manno analogues 3A/3B 95 : 5 and 5A/5B 55 : 45

  酰化和磺酰化Ñ，Ñ ' -未取代的glucosylidenespirodiaziridines 1A / 1B 95：5用Ac 2 O，BzCl，FmocCl，的TsCl，（萘-2-基）磺酰基和（2,4,6-三异丙基）磺酰氯，并伴随重排得到酰化和磺酰化的葡萄糖酸内酯2B - 2G，收率40-83％（方案2）。类似地，半乳和甘露类似物3A / 3B 95：5和5A / 5B 55：45和甘露呋喃基亚砜-二氮丙啶将30个样品乙酰化并甲苯磺酸化，得到4A，4B， 6、31A和31B（55-73％产率；方案2和5）。15的N-二标签11A / 11B和14A / 14B表明的pseudoequatorial NH葡糖二氮丙啶1和的pseudoaxial NH半乳二氮丙啶3被优先乙酰化和甲苯磺酸化（方案3）。N-甲基化二氮丙啶19A / 19B的磺酰化72：28，22A/ 22B 85：15、25A
• Direct Oxidative Amidation of Aldoses by Iodine in Ammonia Water
  作者：Ming-Yi Chen、Jue-Liang Hsu、Jiun-Jie Shie、Jim-Min Fang

  DOI：10.1002/jccs.200300018

  日期：2003.2

  aldohexoses and the benzylated derivatives reacted with iodine in ammonia water at room temperature to give their corresponding saccharide amides in high yields. The reactions proceeded with oxidation of the aldose hemiacetals by iodine to generate the saccharide lactone intermediates, which underwent ammonolysis in situ to give the saccharide amides.

  戊醛糖、己醛糖和苄基化衍生物在室温下与氨水中的碘反应，以高产率得到相应的糖酰胺。反应继续进行，醛糖半缩醛被碘氧化生成糖内酯中间体，该中间体经过原位氨解得到糖酰胺。
• A facile transformation of sugar lactones to azasugars
  作者：Herman S. Overkleeft、Jim van Wiltenburg、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)86715-6

  日期：1994.4

  The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.
• Efficient synthesis of 1-deoxy-azasugars as useful synthetic tools
  作者：Daisuke Sawada、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1016/s0040-4039(03)00512-4

  日期：2003.4

  1-Deoxy-azasugars are efficiently prepared from sugar-lactones using a stereoinversion process and they are applied to the synthesis of a natural product. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Multi gram-scale synthesis of galactothionolactam and its transformation into a galactonoamidine
  作者：Rami Kanso、Susanne Striegler

  DOI：10.1016/j.carres.2011.02.021

  日期：2011.5

  We recently proposed to conduct selective glycosylation reactions after in situ activation of a glycosyl donor promoted by a transition metal complex immobilized in a macromolecular matrix. In order to develop this catalytic entity, a feasible multi gram-scale synthesis for 2,3,4,6-tetra-O-benzyl-D-galactothionolactam, its transformation into galactonoamidines with aromatic aglycon, and subsequent debenzylation conditions were developed. The potential for epimerization reactions at C-2 of the glycosidic ring during the transformations from the 2,3,4,6-tetra-O-benzyl-o-galactonolactam into the N-benzy1-2,3,4,6-tetra-O-benzyl-D-galactonoamidines via the 2,3,4,6-tetra-O-benzyl-D-galactothionolactam are discussed and additionally characterized by using density functional theory calculations. (C) 2011 Elsevier Ltd. All rights reserved.