77870-91-8

Upstream product

• 14464-15-4 methyl 2-(benzyloxycarbonylamino)-3-hydroxypropanoate 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 329365-81-3 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl methanethiosulfonate 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 329365-86-8 ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 82300-58-1 dibezylphosphoryl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 135195-50-5 (S)-2-Benzyloxycarbonylamino-3-trimethylsilanyloxy-propionic acid methyl ester 

Relevant academic research and scientific papers

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

AuCl3- and AuCl3-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature. We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.

Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars

Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5 ? molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic amount of activators.

Glycosyl disulfides: Novel glycosylating reagents with flexible aglycon alteration

Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning strategies.

Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation

A versatile glycosylation reaction is used to establish the process of sulfoxide covalent catalysis. Hemiacetals are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, nBu2SO, for coupling with various nucleophiles (Nu; se

Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups

Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranose to diphenylphosphinic and propane-1,3- diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence of trimethylsilyl triflate (TMSOTf). The use of 1,3-diyl phosphate resulted in the stereoselective formation of β-O-linked glycosides.

Glycosyldisulfides: A new class of solution and solid phase glycosyl donors

Mixed glycosyl disulfides are not only glycomimetics but also glycosyl donors that may be readily constructed in either armed ether-protected or disarmed ester-protected and in soluble or solid-supported forms from corresponding glycosyl methanethiosulfonates and used in the glycosylation of a variety of representative acceptors.

Stereoselective O-glycosylation reactions employing diphenylphosphinate and propane-1,3-diyl phosphate as anomeric leaving groups

Glycosidation of tetra-O-benzyl-D-glucose using diphenylphosphinate as the leaving group afforded β-O-linked glycosides as the major products, whilst the use of propane-1,3-diyl phosphate as the leaving group resulted in the exclusive formation of β-O-lin

O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing Benzyl-Protected Glycosyl Donors

The benzyl-protectd glucosyl trichloroacetimidates, phosphates, and halides 1 are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiCl4 in ether, CH2Cl2, CHCl3, or CH3CN and react under these conditi

New Synthetic Methods and Reagents for Complex Carbohydrates. VII. Syntheses and Glycosylation Reactions of Glycopyranosyl Dimethylphosphinothioate Series Having a Nonparticipating Group at the C-2 Position

Several glycopyranosyl dimethylphosphinothioates having a nonparticipating group at the C-2 position could be easily prepared by reactions of the corresponding glycopyranose and dimethylphosphinothioyl chloride using butyllithium as a base in tetrahydrofu