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

Szabolcs Sipos, I. Jablonkai, O. Egyed, M. Czugler

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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-β-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 β-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.

Original languageEnglish
Pages (from-to)2862-2871
Number of pages10
JournalCarbohydrate Research
Volume346
Issue number18
DOIs
Publication statusPublished - Dec 27 2011

Fingerprint

Acetonitriles
Aldehydes
Aminoacetonitrile
Phenethylamines
Stereochemistry
Sugars
Amines
Carbon

Keywords

  • 1-C-Glycosyl aldehyde
  • 2-Amino-2-C-d-glycosyl- acetonitrile
  • Double asymmetric induction
  • Strecker reaction

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction. / Sipos, Szabolcs; Jablonkai, I.; Egyed, O.; Czugler, M.

In: Carbohydrate Research, Vol. 346, No. 18, 27.12.2011, p. 2862-2871.

Research output: Contribution to journalArticle

@article{f0a50832c11f4758bfb076d9a6ff2b4b,
title = "Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction",
abstract = "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-β-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 β-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.",
keywords = "1-C-Glycosyl aldehyde, 2-Amino-2-C-d-glycosyl- acetonitrile, Double asymmetric induction, Strecker reaction",
author = "Szabolcs Sipos and I. Jablonkai and O. Egyed and M. Czugler",
year = "2011",
month = "12",
day = "27",
doi = "10.1016/j.carres.2011.10.023",
language = "English",
volume = "346",
pages = "2862--2871",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "18",

}

TY - JOUR

T1 - Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction

AU - Sipos, Szabolcs

AU - Jablonkai, I.

AU - Egyed, O.

AU - Czugler, M.

PY - 2011/12/27

Y1 - 2011/12/27

N2 - 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-β-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 β-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.

AB - 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-β-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 β-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.

KW - 1-C-Glycosyl aldehyde

KW - 2-Amino-2-C-d-glycosyl- acetonitrile

KW - Double asymmetric induction

KW - Strecker reaction

UR - http://www.scopus.com/inward/record.url?scp=82155162343&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=82155162343&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2011.10.023

DO - 10.1016/j.carres.2011.10.023

M3 - Article

VL - 346

SP - 2862

EP - 2871

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 18

ER -