3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde | 208585-09-5

• 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: 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde
• 英文别名: (2R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-carbaldehyde
• CAS: 208585-09-5
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: ZBZYPJHJWLRKHH-HPQIJTKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 反应 4.0h， 以99 mg的产率得到ethyl (E)-3-((2R,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)acrylate
  参考文献：
  名称：

  Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity

  摘要：

  一种新颖的方法用于合成萘醌/萘醌醇-碳水化合物混合物，其中Hauser环化反应被描述为关键的合成步骤。

  DOI：

  10.1039/c6ob02154a
• 作为产物：
  描述：

  β-D-glucopyranosyl cyanide 在 吡啶 、 sodium hypophosphite 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde
  参考文献：
  名称：

  Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction

  摘要：

  Synthesis of new 2-amino-2-C-D-glycosyl-acetonitriles in a Strecker reaction from various C-glycosyl aldehydes, chiral amines, and HCN was carried out. While aminonitriles from glycal and 2-deoxy-beta-D-glycosyl aldehydes were prepared in satisfactory yields, lower yields were obtained with C-glycosyl aldehydes. Strecker reaction with the benzyl-protected 1-C-formyl-D-galactal and S- or R-1-phenylethylamine (S-PEA or R-PEA) yielded predominantly the R-configured C-glycosyl aminoacetonitrile. The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with beta-linked sugars. Since the stereochemistry of the transition state is unknown according to the configuration of the major product a Felkin-Ahn selectivity can be mainly presumed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.023

文献信息

• Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction
  作者：Szabolcs Sipos、István Jablonkai、Orsolya Egyed、Mátyás Czugler

  DOI：10.1016/j.carres.2011.10.023

  日期：2011.12

  Synthesis of new 2-amino-2-C-D-glycosyl-acetonitriles in a Strecker reaction from various C-glycosyl aldehydes, chiral amines, and HCN was carried out. While aminonitriles from glycal and 2-deoxy-beta-D-glycosyl aldehydes were prepared in satisfactory yields, lower yields were obtained with C-glycosyl aldehydes. Strecker reaction with the benzyl-protected 1-C-formyl-D-galactal and S- or R-1-phenylethylamine (S-PEA or R-PEA) yielded predominantly the R-configured C-glycosyl aminoacetonitrile. The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with beta-linked sugars. Since the stereochemistry of the transition state is unknown according to the configuration of the major product a Felkin-Ahn selectivity can be mainly presumed. (C) 2011 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity
  作者：Soumen Chakraborty、Gaurav Das、Surajit Ghosh、Dipakranjan Mal

  DOI：10.1039/c6ob02154a

  日期：——

  A novel approach for the synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids using the Hauser annulation as the key synthetic step has been described.

  一种新颖的方法用于合成萘醌/萘醌醇-碳水化合物混合物，其中Hauser环化反应被描述为关键的合成步骤。