Investigation of the H-bond-mediated Aglycone Delivery Reaction in Application to the Synthesis of β-glucosides

Overview

Journal Carbohydr Res

Publisher Elsevier

Specialties Biochemistry
Endocrinology

Date 2018 Oct 5

PMID 30286335

Citations 2

Authors

Michael P Mannino

Jagodige P Yasomanee

Alexei V Demchenko

Affiliations

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Abstract

In an attempt to refine the H-bond-mediated Aglycone Delivery (HAD) glycosylation reaction reported herein is the synthesis of β-glucosides using an ethylthio glucoside donor equipped with the remote 6-O-picoloyl substituent. Upon examining various aliphatic, aromatic, and carbohydrate acceptors, it was determined that both electronic and steric factors may greatly affect the stereoselectivity of the HAD reaction with this donor.

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References

Garegg P, Hultberg H . Synthesis of di- and tri-saccharides corresponding to receptor structures recognised by pyelonephritogenic E. coli fimbriae (pili). Carbohydr Res. 1982; 110(2):261-6. DOI: 10.1016/0008-6215(82)84007-x. View

Yang Y, Zhang X, Yu B . O-Glycosylation methods in the total synthesis of complex natural glycosides. Nat Prod Rep. 2015; 32(9):1331-55. DOI: 10.1039/c5np00033e. View

Yasomanee J, Parameswar A, Pornsuriyasak P, Rath N, Demchenko A . 2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity. Org Biomol Chem. 2016; 14(11):3159-69. DOI: 10.1039/c6ob00107f. View

Escopy S, Geringer S, De Meo C . Combined Effect of the Picoloyl Protecting Group and Triflic Acid in Sialylation. Org Lett. 2017; 19(10):2638-2641. DOI: 10.1021/acs.orglett.7b00976. View

Das R, Mukhopadhyay B . Chemical O-Glycosylations: An Overview. ChemistryOpen. 2016; 5(5):401-433. PMC: 5062006. DOI: 10.1002/open.201600043. View

Ranade S, Kaeothip S, Demchenko A . Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation. Org Lett. 2010; 12(24):5628-31. PMC: 3005820. DOI: 10.1021/ol1023079. View

Liptak M, Gross K, Seybold P, Feldgus S, Shields G . Absolute pK(a) determinations for substituted phenols. J Am Chem Soc. 2002; 124(22):6421-7. DOI: 10.1021/ja012474j. View

Kang J, Kim S, Lee J, Marquez V, Lewin N, Pearce L . Macrocyclic diacylglycerol-bis-lactones as conformationally constrained analogues of diacylglycerol-lactones. Interactions with protein kinase C. J Med Chem. 2004; 47(16):4000-7. DOI: 10.1021/jm0497747. View

Pistorio S, Yasomanee J, Demchenko A . Hydrogen-bond-mediated aglycone delivery: focus on β-mannosylation. Org Lett. 2014; 16(3):716-9. DOI: 10.1021/ol403396j. View

10.

Ruei J, Venukumar P, Ingle A, Mong K . C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation. Chem Commun (Camb). 2014; 51(25):5394-7. DOI: 10.1039/c4cc08465a. View

11.

Zhang F, Zhang W, Zhang Y, Curran D, Liu G . Synthesis and applications of a light-fluorous glycosyl donor. J Org Chem. 2009; 74(6):2594-7. PMC: 2754202. DOI: 10.1021/jo9000993. View

12.

Nukada T, Berces A, Whitfield D . Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor?. Carbohydr Res. 2002; 337(8):765-74. DOI: 10.1016/s0008-6215(02)00043-5. View

13.

Goodman L . Neighboring-group participation in sugars. Adv Carbohydr Chem Biochem. 1967; 22:109-75. DOI: 10.1016/s0096-5332(08)60152-6. View

14.

Yasomanee J, Demchenko A . Effect of remote picolinyl and picoloyl substituents on the stereoselectivity of chemical glycosylation. J Am Chem Soc. 2012; 134(49):20097-102. DOI: 10.1021/ja307355n. View

15.

Yasomanee J, Demchenko A . Hydrogen bond mediated aglycone delivery: synthesis of linear and branched α-glucans. Angew Chem Int Ed Engl. 2014; 53(39):10453-6. DOI: 10.1002/anie.201405084. View

16.

Yasomanee J, Demchenko A . Hydrogen-bond-mediated aglycone delivery (HAD): a highly stereoselective synthesis of 1,2-cis α-D-glucosides from common glycosyl donors in the presence of bromine. Chemistry. 2015; 21(17):6572-81. DOI: 10.1002/chem.201406589. View

17.

Khiar N, Werner S, Mallouk S, Lieder F, Alcudia A, Fernandez I . Enantiopure sulforaphane analogues with various substituents at the sulfinyl sulfur: asymmetric synthesis and biological activities. J Org Chem. 2010; 74(16):6002-9. DOI: 10.1021/jo9007749. View

18.

Wu Y, Tsai Y . Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors. Org Lett. 2017; 19(16):4171-4174. DOI: 10.1021/acs.orglett.7b01658. View

19.

Nigudkar S, Demchenko A . Stereocontrolled 1,2- glycosylation as the driving force of progress in synthetic carbohydrate chemistry. Chem Sci. 2015; 6(5):2687-2704. PMC: 4465199. DOI: 10.1039/C5SC00280J. View

20.

Adero P, Amarasekara H, Wen P, Bohe L, Crich D . The Experimental Evidence in Support of Glycosylation Mechanisms at the S1-S2 Interface. Chem Rev. 2018; 118(17):8242-8284. PMC: 6135681. DOI: 10.1021/acs.chemrev.8b00083. View