157903-83-8

Upstream product

• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 106-95-6 allyl bromide 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 66-99-9 β-naphthaldehyde 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 189144-35-2 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-toluenesulfonyl)-α-D-glucopyranoside 

Downstream Products

• 157903-84-9 3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene 
• 157794-12-2 (2R,3S,4aR,6R,7R,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 157794-06-4 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol 
• 157794-10-0 (2R,3S)-3-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-oxirane-2-carbaldehyde 
• 157794-07-5 (E)-4-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-enoic acid methyl ester 
• 252202-48-5 3-(2'-O-prop-1-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene 
• 157794-05-3 (2R,3S,4R,5R,6R)-2-Allyl-3-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran 
• 189144-29-4 Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester 
• 189144-74-9 C₅₆H₇₄O₂₅ 
• 189144-71-6 C₅₁H₇₀O₂₆ 
• 189144-72-7 C₄₈H₆₆O₂₆ 
• 189144-61-4 Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

METHOD FOR PREPARING HEXOSE DERIVATIVES

A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

Synthesis of kojidextrins and their protein conjugates. Incidence of steric mismatch in oligosaccharide synthesis

Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with α-linked (hydrazinocarbonyl)pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose acceptors failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

Synthesis and Stereochemical Confirmation of the cis-Fused L/M and N/O Ring Systems of Maitotoxin

Stereocontrolled synthesis of cis-fused 1,6-dioxadecalin system 1, which corresponds to the L/M and N/O rings of maitotoxin, was accomplished.Comparison of its (1)H and (13)C NMR data with those of the natural toxin established the earlier stereochemical