benzyl 3,4,6-tri-O-benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-D-glucopyranoside | 1281971-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4,6-tri-O-benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-D-glucopyranoside
• 英文别名: 1,3,4,6-tetra-O-benzyl-2-(tert-butyloxycarbonylamino)-2-deoxy-D-glucopyranoside；1,3,4,6-tetra-O-benzyl-2-(tert-butoxycarbonyl)amino-2-deoxy-D-glucopyranoside；tert-butyl N-[(3R,4R,5S,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 1281971-23-0
• 化学式: C₃₉H₄₅NO₇
• 分子量: 639.789
• InChiKey: OLEMKOKVXHTHBC-VXERKMLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-D-glucopyranoside 在 三氟乙酸 作用下， 生成 1-O-Benzyl-3,4,6-tri-O-benzyl-2-amino-2-deoxy-α,β-D-glucopyranose
  参考文献：
  名称：

  Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane

  摘要：

  A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy-D-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated for their anti-inflammatory activity. Our results showed that all of the compounds tested exhibited a significant inhibition of xylene-induced inflammation in mice. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.062
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 水 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 benzyl 3,4,6-tri-O-benzyl-2-[(tert-butoxycarbonyl)amino]-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Glucosamine-Based Primary Amines as Organocatalysts for the Asymmetric Aldol Reaction

  摘要：

  Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.

  DOI：

  10.1021/jo1023156

文献信息

• Synthesis and Characterization of Monosaccharide Derivatives and Application of Sugar-Based Prolinamides in Asymmetric Synthesis
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1002/ejoc.201200522

  日期：2012.11

  were converted into the corresponding prolinamide organocatalysts (i.e., 1a, 2a, 3a, and 3b) in high yields. The catalytic activity of these sugar-based prolinamide organocatalysts was demonstrated in asymmetric aldol reactions in various solvents and at different temperatures. The oraganocatalyst 3a was shown to be an efficient and powerful organocatalyst for the enantioselective aldol reaction of various

  首次合成、分离和使用N-乙酰氨基葡萄糖衍生物甲基2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷(9b)的β-异头体用于合成糖基伯胺4b。糖基伯胺 5a、一对单糖衍生物 6a 和 6b 以及所有这些化合物的前体也被合成、分离并通过标准光谱方法进行了充分研究，包括 1H-1H COZY 和 HSQC 等 2D NMR 光谱实验. 然后将糖基伯胺 4a、5a、6a 和 6b 以高产率转化为相应的脯氨酰胺有机催化剂（即 1a、2a、3a 和 3b）。这些糖基脯氨酰胺有机催化剂的催化活性在各种溶剂和不同温度下的不对称羟醛反应中得到证明。
• Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane
  作者：Li Zeng、Guichao Xu、Pengchao Gao、Meng Zhang、Hong Li、Jianwei Zhang

  DOI：10.1016/j.ejmech.2015.01.062

  日期：2015.3

  A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy-D-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated for their anti-inflammatory activity. Our results showed that all of the compounds tested exhibited a significant inhibition of xylene-induced inflammation in mice. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Glucosamine-Based Primary Amines as Organocatalysts for the Asymmetric Aldol Reaction
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1021/jo1023156

  日期：2011.5.6

  Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.