Journal
RUSSIAN CHEMICAL BULLETIN
Volume 66, Issue 2, Pages 304-312Publisher
SPRINGER
DOI: 10.1007/s11172-017-1732-9
Keywords
anomeric protective groups; 4-(omega-chloroalkoxy)phenols; phenols; selective demethylation; heterobifunctional building blocks
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Funding
- Russian Foundation for Basic Research [10-03-01019, 13-03-00666, 14-33-50103, 16-03-00755, 16-33-50034]
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Efficient multigram two-step syntheses of 4-(2-chloroethoxy)phenol and 4-(3-chloropropoxy)phenol in > 70% yields starting from 4-hydroxybenzaldehyde and reagents with general formula Cl(CH2) (n) X (X = Cl, n = 2; X = OTs, n = 3) are proposed. 4-(2-Chloroethoxy)phenol can also be conveniently prepared from 4-methoxyphenol and 1,2-dichloroethane. The compounds thus obtained can be used in carbohydrate chemistry to synthesize glycosides bearing universal 4-(omega-chloroalkoxy)phenyl aglycons.
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