3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl formaldehyde | 1320325-11-8

• 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-galactopyranosyl formaldehyde
• 英文别名: (2-deoxy-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)methanal；(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-carbaldehyde
• CAS: 1320325-11-8
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: ZBZYPJHJWLRKHH-BIYDSLDMSA-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-galactopyranosyl formaldehyde 、 (S)-(-)- α-甲基苄胺 、 丙酮氰醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (S)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile 、 (R)-2-[(S)-1-phenylethylamino]-2-C-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)acetonitrile
  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
• 作为产物：
  描述：

  β-D-galactopyranosyl 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-galactopyranosyl 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 1-C-glycosyl aldehydes by reductive hydrolysis
  作者：Szabolcs Sipos、István Jablonkai

  DOI：10.1016/j.carres.2011.04.019

  日期：2011.9

  carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl glycal and 2-deoxy glycosyl derivatives were stable during isolation and storage 1-C-glycosyl formaldehydes in the gluco, galacto and manno series were sensitive and decomposition occurred by 2-alkyloxy elimination

  使用DIBAL-H进行各种保护的糖基氰化物的还原水解以形成醛亚胺铝烷中间体，然后将其在中等酸性条件下水解以提供相应的醛衍生物。尽管1-C-甲酰基糖基和2-脱氧糖基衍生物在分离和存储过程中是稳定的，但葡萄糖，半乳糖和甘露糖系列中的1-C-糖基甲醛很敏感，并且通过2-烷氧基消除发生了分解。开发了一种使用N，N'-二苯基乙二胺以稳定形式捕集这些醛的一锅法。糖基氰化物的还原水解以方便的方式提供了有价值的醛结构单元，可用于合成复杂的C-糖苷。
• 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.