Total synthesis and identification of two diastereoisomers of 1-methyl-2-[N-(p-tolylsulfonyl)-2-pyrrolidinyl]ethyl beta-L-fucopyranoside.
The reaction of a racemic mixture of (2R,2'S)- and (2S,2'R)-N-(p-tolylsulfonyl)-2-pyrrolidinyl-2-propanol, prepared from (S)-proline, with 2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl trichloroacetimidate led to both diastereoisomers of the title compound after O-deacetylation.
E Silva
Maria Joselice
MJ
Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50.740-540 Recife, PE, Brazil.
Cottier
Louis
L
Srivastava
Rajendra M
RM
Sinou
Denis
D
Thozet
Alain
A
D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C502267:1-methyl-2-(N-(4-tolylsulfonyl)-2-pyrrolidinyl)ethyl fucopyranoside; D011759:Pyrrolidines; D005643:Fucose