Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside

Shrestha, Ganesh; Kashiwagi, Gustavo A.; Stine, Keith J.; Demchenko, Alexei V.

doi:10.1016/j.carres.2021.108482

Cited by 5 publications

(2 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methyl 2,4,6-tri- O -benzyl- α -D-glucopyranoside (29) was synthesized as reported previously and its analytical data was in accordance with that previously described [ 25 , 65 ].…”

Section: Methodsmentioning

confidence: 99%

Activation of Thioglycosides with Copper(II) Bromide

Pooladian

Escopy²,

Demchenko³

2022

Molecules

Self Cite

View full text Add to dashboard Cite

Reported herein is a new protocol for glycosidation of alkyl and aryl thioglycosides in the presence of copper(II) bromide. While the activation with CuBr2 alone was proven suitable for reactive glycosyl donors, the activation of less reactive donors was more efficient in the presence of triflic acid as an additive. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this reaction.

show abstract

“…Methyl 2,4,6-tri- O -benzyl- α -D-glucopyranoside (29) was synthesized as reported previously and its analytical data was in accordance with that previously described [ 25 , 65 ].…”

Section: Methodsmentioning

confidence: 99%

Activation of Thioglycosides with Copper(II) Bromide

Pooladian

Escopy²,

Demchenko³

2022

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

“…Our lab has also introduced a number of approaches for the regioselective protection of d -glucose. 2f 15…”

Section: Table 1 Preliminary Screening Of Catalytic Act...mentioning

confidence: 99%

Expedient Synthesis of Superarmed Glycosyl Donors via Oxidative Thioglycosidation of Glycals

Demchenko,

Forsythe,

Mize

et al. 2023

Synthesis

Self Cite

View full text Add to dashboard Cite

Superarmed glycosyl donors have higher reactivity compared to their per-benzylated armed counterparts. Generally, 2-O-benzoyl-3,4,6-tri-O-benzyl protecting group pattern gives rise to increased reactivity rationalized by the O-2/O-5 cooperative effect. Despite having high reactivity profile and applicability in many expeditious strategies for oligosaccharide synthesis, regioselective introduction of the superarming protecting group pattern is tedious for most sugar series. Reported herein is a streamlined synthetic route to yield superarmed glycosyl donors the D-gluco and D-galacto series equipped with ethylthio, phenylthio, tolylthio, S-benzoxazolyl, O-allyl, and O-pentenyl anomeric leaving groups. This streamlined approach was made possible due to the refinement of the oxidative thioglycosylation reaction of the respective glucal and galactal precursors. The applicability of this approach to the direct formation of disaccharides has also been showcased.

show abstract