Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions DOI Creative Commons

Monika Khaleri,

Qingjiang Li

Molecules, Год журнала: 2024, Номер 30(1), С. 120 - 120

Опубликована: Дек. 31, 2024

The rapidly growing glycoscience has boosted the research on synthesis of glycans and their conjugates, which are centered stereoselective formation glycosidic bonds. Compared to mainstream acid-promoted glycosylation method that undergoes S

Язык: Английский

Stereoselective AromaticO-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere DOI
Jinsheng Lai,

Shuqin Wu,

Zhuoyi Zhou

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(15), С. 10721 - 10734

Опубликована: Июль 24, 2023

A novel exclusive β-selective O-aryl glycosylation was developed using glycosyl chloride and arylboronic acid with a palladium catalyst under an air atmosphere. The reaction insensitive to moisture characterized readily available bench-stable as substrates. diverse range of substrate scopes, including various acids donors, well-tolerated in this method. Arylboronic oxidized by O2 produce phenol the aromatic source. This new strategy provides alternative route may find broad applications efficient synthesis bioactive glycosides future.

Язык: Английский

Процитировано

9

Insertion of Glycosylidene Carbenes into Phenolic O–H Bonds for the Synthesis of O-Aryl Glycosides DOI
Qibin Zhu, Xinyu Tian, Gang He

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 18, 2025

We present a new strategy for the synthesis of O-aryl glycosides through formal insertion glycosylidene carbenes into O–H bond phenols. The key carbene intermediates were generated in situ by copper-catalyzed oxidation bench-stable diaziridine precursors. This method enables glycosylation variety phenols with good yields, excellent diastereoselectivity, and chemoselectivity, providing highly practical late-stage complex natural products bioactive agents.

Язык: Английский

Процитировано

0

Studies Concerned with the Structure and Synthesis of the Anti‐viral Tropolone Glycoside Liriosmaside A DOI Creative Commons
Qi Chen,

Yaping Zhan,

Michael G. Gardiner

и другие.

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Апрель 8, 2025

Abstract A bromotropone corresponding to the agylcone of glycosylated sesquiterpenoid natural product liriosmaside has been prepared over ten steps and in a fully regio‐controlled manner through gem ‐dibromocyclopropane‐mediated ring‐expansion readily accessible decalenone. Pd[0]‐mediated glucosylation reaction applied this afforded mixture from which an enantiomerically pure cross‐coupling could be obtained its structure confirmed single‐crystal X‐ray analysis derivative. Various (unsuccessful) attempts are described selectively acylate last compound thereby install 3‐hydroxy‐3‐methylglutaric acid or HMGA‐containing side chain title product. literature survey other products embodying HMGA motif suggest that co‐metabolite B S ‐configured at C3”. The evaluation glucosylated tropone series anti‐bacterial, anti‐fungal cytotoxicity assays reveals it is inactive all these so emphasizing prospect related troponoids, including B, can serve as useful models for new anti‐viral agents.

Язык: Английский

Процитировано

0

Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B DOI
Qi Chen, Martin G. Banwell, Michael G. Gardiner

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-

Язык: Английский

Процитировано

1

Mechanistic Investigation of the Pseudo-Halogen Effect in Enantioselective Aminocatalyzed [6 + 4] and [10 + 6] Cycloadditions: Enabling Unique Favorskii-Like Rearrangements DOI
Casper L. Barløse, René S. Bitsch, Jonas Faghtmann

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 28, 2024

A mechanistic investigation into the novel combination of

Язык: Английский

Процитировано

1

Synthesis of propargyl glycosides of Streptococcus pneumoniae serotypes 6A and 6B for glycoconjugate vaccines DOI

Tianyao Meng,

Brady Davis James,

Jared Haymore

и другие.

Tetrahedron, Год журнала: 2024, Номер 165, С. 134186 - 134186

Опубликована: Авг. 8, 2024

Язык: Английский

Процитировано

0

Highly Regioselective Dehydrogenative Hydrazination of Tropones DOI

Yan Wang,

Muliang Zhang, Shi‐Kai Tian

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 15, 2024

Direct C(sp

Язык: Английский

Процитировано

0

Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions DOI Creative Commons

Monika Khaleri,

Qingjiang Li

Molecules, Год журнала: 2024, Номер 30(1), С. 120 - 120

Опубликована: Дек. 31, 2024

The rapidly growing glycoscience has boosted the research on synthesis of glycans and their conjugates, which are centered stereoselective formation glycosidic bonds. Compared to mainstream acid-promoted glycosylation method that undergoes S

Язык: Английский

Процитировано

0