214068-15-2

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 214068-20-9 methyl 3-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 214068-09-4 methyl 3-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 214068-20-9 methyl 3-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 214068-42-5 Acetic acid (1R,2R,3S,4R,5R,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester 
• 214068-47-0 Phosphoric acid dibenzyl ester (1R,2S,3S,4R,5S,6R)-2,6-bis-benzyloxy-3,5-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester 
• 214068-38-9 Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 214068-22-1 methyl 3-O-(p-methoxybenzyl)-2,4-O-dibenzyl-6-O-trityl-α-D-glucopyranoside 
• 214068-40-3 Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester 
• 194207-33-5 methyl (Z)-2,4-O-dibenzyl-3-O-(p-methoxybenzyl)-6-O-acetyl-α-D-glucos-5-enopyranoside 
• 214068-35-6 Acetic acid (1R,2R,3S,4R,5S)-3,5-bis-benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester 
• 214332-47-5 Acetic acid (1R,2R,3S,4R,5R,6R)-3,5-bis-benzyloxy-2,6-dihydroxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 194207-17-5 methyl 3-O-(p-methoxybenzyl)-2,4-O-dibenzyl-α-D-glucopyranoside 
• 194207-24-4 (2S,3S,4S,5R,6S)-3,5-Bis-benzyloxy-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 

Relevant academic research and scientific papers

CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups

CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis.

Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsPn derivatives with diacylglyceryl moieties of different chain lengths.