An expeditious route to N-Acetyl-D-galactosamine from N-Acetyl-D- glucosamine based on the selective protection of hydroxy groups

Naoyuki Ito, Yoshihide Tokuda, Shigeru Ohba, Takeshi Sugai

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

GalNAc (1) was straightforwardly prepared from GlcNAc (2a) in six steps. Selective protection of the hydroxy groups on the C-1, C-3, and C-6 positions at the same time was performed by the treatment of TBDPS chloride (5.5 eq.) in DMF in 70% yield. The nucleophilic attack with CsOAc or KOBz on the chloromethylsulfonyloxy group at C-4 worked well (69-77% yield), accompanied by an unexpected rearrangement, to give the furanose products (6). The deprotection of all silyl and acyl groups under acidic conditions and the re-acetylation provided GalNAc (1) in 51% yield.

Original languageEnglish
Pages (from-to)1181-1186
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number6
DOIs
Publication statusPublished - 2004

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Acetylgalactosamine
Acetylation
Acetylglucosamine
Chlorides

ASJC Scopus subject areas

  • Chemistry(all)

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An expeditious route to N-Acetyl-D-galactosamine from N-Acetyl-D- glucosamine based on the selective protection of hydroxy groups. / Ito, Naoyuki; Tokuda, Yoshihide; Ohba, Shigeru; Sugai, Takeshi.

In: Bulletin of the Chemical Society of Japan, Vol. 77, No. 6, 2004, p. 1181-1186.

Research output: Contribution to journalArticle

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