More than a protective group: 4-methoxyphenyl as a new Janus aglycone

More than a protective group: 4-methoxyphenyl as a new Janus aglycone Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2025, Volume: 554, Article number : 109544, Pages count : DOI: 10.1016/j.carres.2025.109544

Authors

Novosad Bogdan L ¹ , Zinin Alexander I ¹ , Chizhov Alexander O ¹ , Kononov Leonid O ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991, Moscow, Russian Federation

4-Methoxyphenyl (MP) aglycone has been widely used as an anomeric protective group (orthogonal to many other frequently used protective groups) during syntheses of various oligosaccharides. We studied the cleavage of the methyl group in MP aglycone under acidic and basic conditions and found that under optimized conditions (EtSH, NaOH, N-methylpyrrolidone, 130 °C) the target glycosides (either protected or unprotected) with 4-hydroxyphenyl (HP) aglycone can be prepared in preparative yields approaching ∼90 % for (partially) protected HP glycosides and ∼80 % for unprotected HP glycosides. Subsequent substitution of the phenolic hydroxy group in the obtained HP glycosides with various alkylating agents efficiently gave the corresponding glycosides with various functional groups in aglycone. The results obtained suggest that the MP aglycone can be considered as a cleavable pre-spacer aglycone, thereby expanding the family of Janus aglycones.

Novosad B.L. , Zinin A.I. , Chizhov A.O. , Kononov L.O.
More than a protective group: 4-methoxyphenyl as a new Janus aglycone
Carbohydrate Research. 2025. V.554. 109544 . DOI: 10.1016/j.carres.2025.109544 WOS Scopus OpenAlex

Web of science:	WOS:001501639700002
Scopus:	2-s2.0-105006742615
OpenAlex:	W4410593209

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OpenAlex	1
Web of science	1
Scopus	1