116142-80-4

Upstream product

• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 134160-64-8 4',5'-epoxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 108-24-7 acetic anhydride 
• 145383-38-6 methyl O-<3,4,6-tri-O-acetyl-2-deoxy-(2,2,2-trichloroethoxycarbonyl)amino)-β-D-glucopyranosyl>-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 
• 187455-96-5 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-ethylsulfanyl-tetrahydro-pyran-4-yl ester 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 144923-59-1 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 

Downstream Products

• 111462-66-9 β-D-GlcpNAc-(1->6)-α-D-Manp-OMe 

Relevant academic research and scientific papers

Direct and stereoselective synthesis of 2-acetamido-2-deoxy-β-D- glycopyranosides by using the phosphite method

(Chemical Equation Presented) Avoiding the intermediate: The β-selective glycosidation of 2-acetamido-2-deoxyglycosyl diethyl phosphites promoted by bis(trifluoromethanesulfonyl)imide (Tf2NH) proceeds in a direct manner and does not afford an o

Chemoselective synthesis of oligosaccharides of 2-deoxy-2-aminosugars

(Chemical Equation Presented) Along with the application of the S-benzoxazolyl glycosides to the high-yielding synthesis of disaccharides of the 2-amino-2-deoxy series, chemoselective assembly of oligosaccharides containing multiple residues of 2-amino-2-

Dual-participation protecting group solves the anomeric stereocontrol problems in glycosylation reactions

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions

Carbohydrates are involved in nearly all aspects of biochemistry, but their complex chemical structures present long-standing practical challenges to their synthesis. In particular, stereochemical outcomes in glycosylation reactions are highly dependent on the steric and electronic properties of coupling partners; thus, carbohydrate synthesis is not easily predictable. Here we report the discovery of a macrocyclic bis-thiourea derivative that catalyzes stereospecific invertive substitution pathways of glycosyl chlorides. The utility of the catalyst is demonstrated in the synthesis of trans-1,2-, cis-1,2-, and 2-deoxy-β-glycosides. Mechanistic studies are consistent with a cooperative mechanism in which an electrophile and a nucleophile are simultaneously activated to effect a stereospecific substitution reaction.

Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method

A direct construction of 1,2-trans-β-linked 2-acetamido-2-deoxyglycosides was investigated. The 3,4,6-tri-O-benzyl- and 3,4,6-tri-O-acetyl-protected glycosyl diethyl phosphites and 4,6-O-benzylidene-protected galactosyl diethyl phosphite each reacted with

Highly selective formation of β-glycosides of N-acetylglucosamine using catalytic iron(III) Triflate

Efficient and highly selective glycosylation reactions of peracetylated β-D-N-acetylglucosamine are described using catalytic iron(III) triflate and 2,4,6-tri-tert-butylpyrimidine (TTBP) under microwave conditions. We have demonstrated that the formation of β-(1→6) and β-(1→3) linked disaccharides are obtained in high yields in the presence ofvarious protecting groups.

H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions

N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of βglycosides of N-acetyl glycosylamines from easily accessible perO-ac

A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate

p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 °C in CH2Cl2.

Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates

A direct, mild and efficient protocol for the preparation of β-glycosides of N-acetyl glucosamine (GlcNAc) and N-acetyl galactosamine (GalNAc) has been developed using peracetylated β-GlcNAc and β-GalNAc as donors. All rare Earth metal triflate promoters

New diacylamino protecting groups for glucosamine

Glucosamine was 'transformed into N-diphenylmaleoyl (DPM), N-(3,3-dimethylglutaryl) (DMG), and N-diglycolyl (DG) derivatives which furnished O-acetyl-protected O-glycosyl trichloroacetimidates 3, 12, and 20, respectively, as glycosyl donors. Their reactio