The synthesis of diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride.
The N-trifluoroacetyl- and N-tetrachlorophthaloyl-protected bromide of D-glucosamine has been used for the first time as a glycosyl donor for the glycosylation of diosgenin [(25R)-spirost-5-en-3beta-ol]. Both 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-beta-D-glucopy ranoside and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha,beta -D-glucopyranoside were transformed into the appropriate glycosyl bromides. These reacted with diosgenin under mild conditions, using silver triflate as a promoter, and gave the corresponding protected diosgenyl glycosides. Each was deprotected to give diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride. The structures of the new glycosides were established by 1H NMR spectroscopy.
Bednarczyk
D
D
Faculty of Chemistry, University of Gdańsk, Poland.
Kaca
W
W
Myszka
H
H
Serwecińska
L
L
Smiatacz
Z
Z
Zaborowski
A
A
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004144:Diosgenin / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005944:Glucosamine / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008214:Lymphocytes / Q000187:drug effects; D008223:Lymphoma / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013150:Spirostans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D006027:Glycosides; D013150:Spirostans; C420652:diosgenyl 2-amino-2-deoxy-glucopyranoside; D004144:Diosgenin; D005944:Glucosamine