“One-pot” protection, glycosylation, and protection–glycosylation strategies of carbohydrates

SS Kulkarni, CC Wang, NM Sabbavarapu… - Chemical …, 2018 - ACS Publications
Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play
significant roles in a variety of vital biological processes. Access to unique and …

Glycosylation with sulfoxide-based glycosyl donors

P Wu, J Zeng, L Meng, Q Wan - Chemical Communications, 2024 - pubs.rsc.org
Sulfoxides have emerged as pivotal constituents in modern carbohydrate chemistry. As
anomeric leaving groups, sulfinyl moieties may occupy positions directly at the anomeric …

One-pot relay glycosylation

X Xiao, J Zeng, J Fang, J Sun, T Li, Z Song… - Journal of the …, 2020 - ACS Publications
A novel one-pot relay glycosylation has been established. The protocol is characterized by
the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This …

Synthesis and stereocontrolled equatorially selective glycosylation reactions of a pseudaminic acid donor: Importance of the side-chain conformation and …

B Dhakal, D Crich - Journal of the American Chemical Society, 2018 - ACS Publications
Pseudaminic acid is an amino deoxy sialic acid whose glycosides are essential components
of many pathogenic Gram-negative bacterial cell walls including those from Pseudomonas …

Application of interrupted Pummerer reaction mediated (IPRm) glycosylation in natural product synthesis

X Zhao, J Zeng, L Meng, Q Wan - The Chemical Record, 2020 - Wiley Online Library
Although numerous glycosylation methods have been developed for the construction of
glycosidic bonds, the pace of discovering rapid assembly strategies to access complex …

Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors

KD Lacey, RD Quarels, S Du, A Fulton, NJ Reid… - Organic …, 2018 - ACS Publications
Two classes of thioglycoside, 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-
(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O …

MPTGs: Thioglycoside Donors for Acid-Catalyzed O-Glycosylation and Latent-Active Synthetic Strategies

S Du, JR Ragains - Organic letters, 2019 - ACS Publications
4-(p-Methoxyphenyl)-4-pentenylthioglycosides (MPTGs) undergo acid-catalyzed O-
glycosylation with a range of alcohol acceptors in the presence of 10 mol% of triflic acid at …

Indolylthio glycosides as effective building blocks for chemical glycosylation

G Shrestha, M Panza, Y Singh, NP Rath… - The Journal of …, 2020 - ACS Publications
The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be
activated for chemical glycosylation under a variety of conditions including thiophilic and …

Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor

Z Zheng, L Zhang - Carbohydrate research, 2019 - Elsevier
Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor
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A Mild Glycosylation Protocol with Glycosyl 1‐Methylimidazole‐2‐carboxylates as Donors

J Chen, Y Tang, B Yu - European Journal of Organic Chemistry, 2021 - Wiley Online Library
A mild glycosylation protocol is developed by using glycosyl 1‐methylimidazole‐2‐
carboxylates. Such a glycosylation can be promoted by a series of metal triflates and …