Highly alpha-selective synthesis of sialyl spirohydantoins by regiospecific domino condensation/O-->N acyl migration/N-sialylation of carbodiimides with peracetylated sialic acid

Dengyou Zhang; Deju Ye; Enguang Feng; Jinfang Wang; Jianmei Shi; Hualiang Jiang; Hong Liu

doi:10.1021/jo100016k

Highly alpha-selective synthesis of sialyl spirohydantoins by regiospecific domino condensation/O-->N acyl migration/N-sialylation of carbodiimides with peracetylated sialic acid

J Org Chem. 2010 Jun 4;75(11):3552-7. doi: 10.1021/jo100016k.

Authors

Dengyou Zhang¹, Deju Ye, Enguang Feng, Jinfang Wang, Jianmei Shi, Hualiang Jiang, Hong Liu

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China.

PMID: 20462259
DOI: 10.1021/jo100016k

Abstract

A novel and efficient process for the synthesis of alpha-sialyl spirohydantoin analogues via one-pot sequential reaction involving various carbodiimides and peracetylated Neu5Ac is reported. BF(3) x Et(2)O mediating intramolecular N-sialylation with excellent alpha-selectivity is first demonstrated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylation
Carbodiimides / chemistry*
Hydantoins / chemical synthesis*
Organic Chemistry Phenomena
Sialic Acids / chemistry*
Spiro Compounds / chemistry

Substances

Carbodiimides
Hydantoins
Sialic Acids
Spiro Compounds