73415-91-5

Upstream product

• 97204-75-6 (Z)-(2R,3R,4R)-6-methoxy-1,3,4-tribenzyloxy-5-hexen-2-ol 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 148926-05-0 methyl 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranoside 
• 128-08-5 N-Bromosuccinimide 
• 161664-82-0 ethyl 3,4,6-tri-O-benzyl-2-O-(methoxy isopropylidene)-1-thio-α-D-mannopyranoside 
• 40246-31-9 methyl 3,4,6-tri-O-benzyl-β-D-arabinohexopyranoside-2-ulose 
• 1067-52-3 tributyltin methoxide 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 74-88-4 methyl iodide 
• 104652-37-1 3,4,6-tri-O-benzyl-2-O-benzylsulfonyl-β-D-mannopyranose 
• 104684-56-2 3,4,6-tri-O-benzyl-2-O-benzylsulfonyl-α-D-mannopyranosyl chloride 
• 301645-80-7 phenyl 2-O-(prop-1-enyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 81644-97-5 3,4,6-tri-O-benzyl-2-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-β-L-rhamnopyranosyl)-α-D-glucopyranoside 
• 81644-98-6 3,4,6-tri-O-benzyl-2-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 
• 73445-29-1 methyl 2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 77770-58-2 methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside 
• 76491-21-9 Methyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-manno-hexopyranoside 
• 58341-63-2 methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 129948-14-7 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 163668-93-7 2-benzyloxy-1,3-bis(methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosid-2-O-yl)propane 
• 163668-86-8 methyl 2-O-(3-allyloxy-2-benzyloxypropyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses

- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.

Stereoselective β-mannosylation via anomeric O-alkylation: Formal synthesis of potent calcium signal modulator acremomannolipin A

Stereoselective β-mannosylation has been investigated via cesium carbonate-mediated anomeric O-alkylation of D-mannose-derived lactol with various electrophiles. It was found that electrophiles bearing trifluoromethanesulfonate (triflate) as the leaving g

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Triisobutylaluminium and dusobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins

To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then induces the regioselectivity of the de-O-alkylation by coordinating preferentially to one of the oxygen atoms of the selected pair.

Experimental evidence on the hydroxymethyl group conformation in alkyl β-D-mannopyranosides

A rotational population study of the hydroxymethyl group of alkyl β-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl β-D-mannopyranosides with different chiral and non

Allyl protecting group mediated intramolecular aglycon delivery: Optimisation of mixed acetal formation and mechanistic investigation

An efficient protocol for the formation of α-iodo mixed acetals, the first step of allyl-mediated IAD, by reaction of allyl-derived enol ethers and alcohols, using I2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, i

Trimethylaluminium promoted rearrangements of unsaturated sugars into cyclohexanes

Trimethylaluminium induces a stereoselective rearrangement of unsaturated glycosides into polyfunctionalised cyclohexanic rings containing a tertiary alcohol and retaining the anomeric group. In contrast with the previously used triisobutylaluminium, no de-O-benzylation reaction was observed.

Stereoselective 1,2-cis glycosylation of 2-O-Allyl protected thioglycosides

The technique of intramolecular aglycon delivery (IAD), whereby a glycosyl acceptor is temporarily appended to a hydroxyl group of a glycosyl donor is an attractive method that can allow the synthesis of 1,2-cis glycosides in an entirely stereoselective f

Allyl protecting group mediated intramolecular aglycon delivery (IAD) of glycosyl fluorides

Stereospecific 1,2-cis-glycosylation of 2-O-allyl protected glucosyl and mannosyl fluorides can be achieved via a sequence of allyl isomerization, N-iodosuccinimide mediated tethering, and intramolecular aglycon delivery (IAD). Fluoride is advantageous as

N-Iodosuccinimide-mediated intramolecular aglycon delivery

Enol ethers may be accessed via Tebbe methylenation of either 2-O acetates or para-methoxybenzoates. N-Iodosuccinimide may then be employed to achieve both tethering and thioglycoside activation allowing the stereoselective synthesis of α-glucosides and β-mannosides, either in a one or two step procedure.