Site-selective carbamoylation of carbohydrates catalyzed by SnCl2/Me2SnCl2leading to complementary selectivity

Guo, Yang-Fan; Luo, Tao; Dong, Hai

doi:10.1039/d3qo00607g

Cited by 2 publications

(1 citation statement)

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“…Acylation, especially acetylation, of the saccharide hydroxyl group is among the most commonly used protection strategies in carbohydrate chemistry because the acyl group is convenient to achieve protection and deprotection. Albeit far from being perfect, regioselective acylation of the carbohydrate hydroxyl group has long been pursued and investigated, which was often achieved under catalytic conditions using organotins, organoborons, metal salts, N -bearing organic bases, and lipases as catalysts.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)

Chen,

Wei,

Cheng

et al. 2024

J. Org. Chem.

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A general approach for regioselective deacetylation at sugar 3-OH of peracetylated 6-deoxy-C-glucopyranosides mediated by BCl 3 was developed. The approach could be extended to other sugar-derived 6-deoxy-C-glycopyranosides, such as those derived from mannose, galactose, and rhamnose, with deacetylation occurring at varied sugar hydroxyl groups, and further extended to 4-deoxy-C-glucopyranosides with deacetylation occurring at sugar 3-OH. The approach would enable access to synthetically challenging carbohydrate derivatives. A possible mechanism of the regioselectivity was proposed.

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Section: Introductionmentioning

confidence: 99%

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)

Chen,

Wei,

Cheng

et al. 2024

J. Org. Chem.

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Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

Guo,

Yu,

Dong

2024

J. Org. Chem.

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In this study, we systematically investigated the regioselective glycosylation of 2,4-OH mannoside and galactoside acceptors since regioselective protection of their 3- and 6-OHs is readily achieved. By altering the protecting groups at 1-, 3-, and 6-positions of such acceptors, we finally screened p-methoxyphenyl 3-OBn, 6-OTBDPS, α-mannoside, and β-galactoside acceptors whose 2-OHs exhibited excellent selectivity for glycosylation with various glycosyl donors, leading to 1,2-linked products in 70–82% yields. By utilizing such acceptors, a series of 2,4-linked trisaccharide products (53–65% yields over two steps) have been highly efficiently synthesized without the need for complex protection/deprotection operations at the 2- and 4-positions of these acceptors.

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Site-selective carbamoylation of carbohydrates catalyzed by SnCl₂/Me₂SnCl₂leading to complementary selectivity

Abstract: This work reports SnCl2/Me2SnCl2-catalyzed site-selective carbamoylation of carbohydrates with a broad substrate scope, associated with mild reaction conditions, good selectivity and high isolated yields (using flash column). In particular, the...

Cited by 2 publications

References 29 publications

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)

Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

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Site-selective carbamoylation of carbohydrates catalyzed by SnCl2/Me2SnCl2leading to complementary selectivity

Abstract: This work reports SnCl2/Me2SnCl2-catalyzed site-selective carbamoylation of carbohydrates with a broad substrate scope, associated with mild reaction conditions, good selectivity and high isolated yields (using flash column). In particular, the...

Cited by 2 publications

References 29 publications

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3)

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3)

Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

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Site-selective carbamoylation of carbohydrates catalyzed by SnCl₂/Me₂SnCl₂leading to complementary selectivity

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)

Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl₃)