Enantiocontrolled Synthesis of the Antifungal β-Lactam (2R, 5S)-2-(Hydroxymethyl)clavam

The antifungal β-lactam (2R, 5S)-2-(hydroxymethyl)clavam was synthesized in a convergent and stereocontrolled manner from methyl 6-phthalimidopenicillanate and 2, 3-O-isopropylidene-(R)-glyceraldehyde. Convenient methods of acetonide cleavage and phthalimide deblocking are also described.

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 39; no. 9; pp. 2212 - 2215
Main Authors KONOSU, Toshiyuki, OIDA, Sadao
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.01.1991
Pharmaceutical Soc Japan
Maruzen
Subjects
(2R, 5S)-2-(hydroxymethyl)clavam
acetonide
antifungal
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
deblocking
diozotization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Life Sciences & Biomedicine
Organic chemistry
oxapenam
Pharmacology & Pharmacy
phthalimide
Physical Sciences
Preparations and properties
Science & Technology
synthesis
β-lactam
(2R,5S)-2-(HYDROXYMETHYL)CLAVAM
CLAVAM ANTIBIOTICS
ACETONIDE
DEBLOCKING
2 VARIANTS
BETA-LACTAM
DIAZOTIZATION
RO-22-5417
HYGROSCOPICUS
SYNTHESIS
FERMENTATION
OXAPENAM
PHTHALIMIDE
STREPTOMYCES-CLAVULIGERUS
ANTIFUNGAL
Stereoselectivity
Bicyclic compound
Antifungal agent
Lactam
Primary alcohol
Oxygen nitrogen heterocycle
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Summary:The antifungal β-lactam (2R, 5S)-2-(hydroxymethyl)clavam was synthesized in a convergent and stereocontrolled manner from methyl 6-phthalimidopenicillanate and 2, 3-O-isopropylidene-(R)-glyceraldehyde. Convenient methods of acetonide cleavage and phthalimide deblocking are also described.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.39.2212