Efficient synthesis of α-galactosylceramide and its C-6 modified analogs

The synthesis of α-galactosylceramide (KRN7000) and its C-6 modified analogs remains a challenge due to the difficult α-1,2-cis-glycosidic bond. A non-participating benzyl (Bn) protecting group has been commonly used to favor the α-glycosylation product. Here, we report the α-selective glycosylation...

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Autores principales: Li, Huiting, Mao, Hongzhao, Chen, Chao, Xu, Ying, Meng, Shuai, Sun, Tiantian, Zong, Chengli
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9732566/
https://www.ncbi.nlm.nih.gov/pubmed/36505742
http://dx.doi.org/10.3389/fchem.2022.1039731
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author Li, Huiting
Mao, Hongzhao
Chen, Chao
Xu, Ying
Meng, Shuai
Sun, Tiantian
Zong, Chengli
author_facet Li, Huiting
Mao, Hongzhao
Chen, Chao
Xu, Ying
Meng, Shuai
Sun, Tiantian
Zong, Chengli
author_sort Li, Huiting
collection PubMed
description The synthesis of α-galactosylceramide (KRN7000) and its C-6 modified analogs remains a challenge due to the difficult α-1,2-cis-glycosidic bond. A non-participating benzyl (Bn) protecting group has been commonly used to favor the α-glycosylation product. Here, we report the α-selective glycosylation by using a bulky 4,6-O-di-tert-butylsilylene (DTBS) galactosyl donor, regardless of the 2-benzoyl (Bz) participating group. Compared with Bn, Bz groups can be selectively removed in basic conditions without impacting the C-6 azide modification. The azide has the potential for clicking with alkyne or being easily transformed to other functional groups.
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spelling pubmed-97325662022-12-10 Efficient synthesis of α-galactosylceramide and its C-6 modified analogs Li, Huiting Mao, Hongzhao Chen, Chao Xu, Ying Meng, Shuai Sun, Tiantian Zong, Chengli Front Chem Chemistry The synthesis of α-galactosylceramide (KRN7000) and its C-6 modified analogs remains a challenge due to the difficult α-1,2-cis-glycosidic bond. A non-participating benzyl (Bn) protecting group has been commonly used to favor the α-glycosylation product. Here, we report the α-selective glycosylation by using a bulky 4,6-O-di-tert-butylsilylene (DTBS) galactosyl donor, regardless of the 2-benzoyl (Bz) participating group. Compared with Bn, Bz groups can be selectively removed in basic conditions without impacting the C-6 azide modification. The azide has the potential for clicking with alkyne or being easily transformed to other functional groups. Frontiers Media S.A. 2022-11-25 /pmc/articles/PMC9732566/ /pubmed/36505742 http://dx.doi.org/10.3389/fchem.2022.1039731 Text en Copyright © 2022 Li, Mao, Chen, Xu, Meng, Sun and Zong. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Li, Huiting
Mao, Hongzhao
Chen, Chao
Xu, Ying
Meng, Shuai
Sun, Tiantian
Zong, Chengli
Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title_full Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title_fullStr Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title_full_unstemmed Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title_short Efficient synthesis of α-galactosylceramide and its C-6 modified analogs
title_sort efficient synthesis of α-galactosylceramide and its c-6 modified analogs
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9732566/
https://www.ncbi.nlm.nih.gov/pubmed/36505742
http://dx.doi.org/10.3389/fchem.2022.1039731
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