Preparation of aminosaccharides using ester-imine condensations: syntheses of methyl N-benzoylacosaminide and methyl N-[oxo(phenylmethoxy) acetyl)daunosaminide from (S)-ethyl 3-hydroxybutyrate

Judith C. Gallucci, Deok-Chan Ha, David J. Hart

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).

Original languageEnglish
Pages (from-to)1283-1292
Number of pages10
JournalTetrahedron
Volume45
Issue number5
Publication statusPublished - 1989 Dec 1
Externally publishedYes

Fingerprint

Lactams
Imines
Condensation
Esters
Hydroxybutyrates
Pyrans
Derivatives
ethyl 3-hydroxybutyrate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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abstract = "The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).",
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T1 - Preparation of aminosaccharides using ester-imine condensations

T2 - syntheses of methyl N-benzoylacosaminide and methyl N-[oxo(phenylmethoxy) acetyl)daunosaminide from (S)-ethyl 3-hydroxybutyrate

AU - Gallucci, Judith C.

AU - Ha, Deok-Chan

AU - Hart, David J.

PY - 1989/12/1

Y1 - 1989/12/1

N2 - The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).

AB - The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).

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