Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides | Zendy

Kundu Monalisa | Zendy; Misra Anup Kumar | Zendy

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Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides

Author(s) -

Kundu Monalisa,

Misra Anup Kumar

Publication year - 2021

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202100606

Subject(s) - glycosyl , chemistry , anomer , alkyl , carbon disulfide , yield (engineering) , aryl , sulfide , organic chemistry , disulfide bond , combinatorial chemistry , medicinal chemistry , biochemistry , materials science , metallurgy

A significantly fast one step reaction condition has been developed for the synthesis of unsymmetrical anomeric glycosyl disulfide derivatives in excellent yield by the treatment of anomeric glycosyl bromides with a combination of carbon disulfide (CS 2 ) and sodium sulfide nonahydrate (Na 2 S ⋅ 9H 2 O) in the presence of symmetrical alkyl, aryl and glycosyl disulfides at room temperature. Exclusive formation of anomerically beta‐disulfides was observed under the reaction conditions. Most of the reactions are high yielding and suitable for scale‐up synthesis.

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