120312-13-2

Upstream product

• 200938-30-3 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 475650-96-5 4-O-allyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranosyl fluoride 
• 151992-76-6 Ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 151992-75-5 ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 120312-10-9 tert-Butyldimethylsilyl-4-O-allyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 120312-00-7 4-O-allyl-2-azido-3,6-di-O-benzyl-2-desoxy-D-glucopyranose 
• 120312-07-4 tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 120312-08-5 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 120312-09-6 tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 99049-68-0 tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid 
• 166516-68-3 ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 129519-27-3 2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 

Downstream Products

• 200938-37-0 Phosphoric acid (1R,2R,3S,4R,5R,6R)-2-((2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrahydroxy-cyclohexyl ester dibenzyl ester 
• 129210-15-7 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 

Relevant academic research and scientific papers

First total synthesis of a GPI-anchored peptide

A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoeth-anolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.

Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

Short synthetic routes to protected derivatives of 2-amino-2-deoxy-α-D-glucopyranosyl-(1→6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting from D-glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3- D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances.

Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors

Synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate, an inner core structure found in various glycosylphosphatidylinositols, and the corresponding 1,2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides bound to the 4-position of the glucosamine unit. The phosphorylation was accomplished by the phosphoramidate procedure.

Glycosyl Imidates, 41. - 6-O-Benzyl-Protected Muramic Acid as Glycosyl Acceptor. - Synthesis of the GlcNAc-β-(1->4)MurNAc Disaccharide

The α-trichloroacetimidates 1 and 2 as glucosamine donors afford with the 6-O-benzyl-protected muramic acid 6a as acceptor the β-connected disaccharides 14 and 15, respectively, in high yields.Compound 14 furnishes by cleavage of the TBDMS group, transfor