1332305-10-8

Basic information

• Product Name: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serinate
• Synonyms: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serinate
• CAS NO: 1332305-10-8
• Molecular Weight: 907.928
• Mol File: 1332305-10-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serinate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serinate(1332305-10-8)
• EPA Substance Registry System: benzyl N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serinate(1332305-10-8)

Safety Data

• Hazardous Substances Data: 1332305-10-8(Hazardous Substances Data)

Upstream product

• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 250273-77-9 1,2-Di-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 853308-49-3 phthalimidyl-2,3,4,6-tetra-O-benzoyl-β-d-glucopyranoside 

Downstream Products

• 1332305-09-5 O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-N-carboxy-L-serine anhydride 
• 1053271-25-2 per-O-benzoylated-β-D-glucose-L-serine 

Relevant articles and documents

Triflic Imide-Catalyzed Glycosylation of Disarmed Glycosyl ortho-Isopropenylphenylacetates and ortho-Isopropenylbenzyl Thioglycosides

Glycosylation reaction involving the coupling of a glycosyl donor with a glycosyl acceptor is one of the cornerstones of chemical preparation of pure glycans and glycoconjugates of biological relevance. Catalytic glycosylation of glycosyl ester donors and thioglycosides is an attractive but underexplored topic in carbohydrate chemistry. Herein, triflic imide (Tf2NH)-catalyzed glycosylation of various O-, S-, and C-nucleophiles has been achieved using disarmed glycosyl ortho-isopropenylphenylacetates (GIPPAs) and ortho-isopropenylbenzyl thioglycosides as glycosylating agents. The reactions proceed under mild conditions to give the desired glycosides in good-to-excellent yields. Of particular note, the comparable reactivity for the α-isomers and the β-ones of GIPPAs is observed. The mechanistic investigation demonstrates that the isopropenyl group is essential for the reaction and its preferential protonation triggers the reaction. This work provides another member to the arsenals of glycosyl ester and thioglycoside donors suitable for acid-catalyzed glycosylation to create various glycosidic bonds.

Isoquinoline-1-Carboxylate as a Traceless Leaving Group for Chelation-Assisted Glycosylation under Mild and Neutral Reaction Conditions

Glycosyl isoquinoline-1-carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction was promoted by the inexpensive Cu(OTf)2 salt under mild reaction conditions. The copper isoquinoline-1-carboxylate salt was precipitated from the solution and thus rendered a traceless leaving group. Surprisingly, the proton from the acceptor was absorbed by the precipitated metal complex and the reaction mixture remained at neutral pH. The copper-promoted glycosylation was also proven to be completely orthogonal to the gold-promoted glycosylation, and an iterative synthesis of oligosaccharides from benchtop stable anomeric ester building blocks becomes possible under mild reaction conditions.

Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors

Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-trans glycosides in good yields under AuBr3/4 A MS Powder/CH2Cl2/rt. t-Boc serine derivative gave serine 1,2-orthoester and glycosyl carbamate. Optimized conditions enabled preparation of new glycosyl carbamates from N-Boc protected amines in a single step using gold catalysts and propargyl 1,2-orthoesters in excellent yields.