Thiosugars. II. Rearrangement of 2-(3,4,6-Tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl)-2-thiop seudourea ^1a,b

Journal Article · Thu Feb 28 23:00:00 EST 1963 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo01038a065· OSTI ID:4628672

Wolfrom, M. L.; Horton, D.; Hutson, D. H.

In neutral solution 2-(3,4,6-tri-O-acetyl-2-amino-2deoxy- BETA -D- glucopyranosyl)-2-thiopseudourea dihydrobromide (I) undergoes rearrangement to form 3,4,6-tri-Oacetyl-2-deoxy-2-guanidino-l-thio-D-glucose (III). A product from the acetylation of I in acidic solution was identical with 1,3-di-N-acetyl-2- (2-acetamido-3,4,6-triO-acetyl-2-deoxy- BETA -D- glucopyrano syl)-2 - thiopseudourea (II), which was prepared by acetylation of 2-(2-acetamido3,4, 6- tri-O-acetyl -2-deoxy - BETA - D-glucopyranosyl)-2thiopseudourea hydrochloride (IV). The behavior of I and related derivatives on desulfurization is discussed. (auth)

• Research Organization: Ohio State Univ., Columbus
• Sponsoring Organization: USDOE
• NSA Number: NSA-17-039087
• OSTI ID: 4628672
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 3 Vol. 28; ISSN 0022-3263
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ACETIC ACID
ACETYL RADICALS
ACETYLATION
ACIDITY
BROMIDES
CHEMICAL REACTIONS
CHEMISTRY
GUANIDINE
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
SOLUTIONS
SUGARS