214068-24-3

Upstream product

• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 214068-17-4 methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 214068-00-5 methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 
• 214068-12-9 methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 1054640-17-3 (2S,3S,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 
• 214068-33-4 Acetic acid (1R,3S,4R,5S,6R)-3,4-bis-benzyloxy-6-hydroxy-5-(4-methoxy-benzyloxy)-2-oxo-cyclohexyl ester 
• 214068-28-7 methyl (Z)-3,4-O-dibenzyl-2-O-(p-methoxybenzyl)-6-O-acetyl-α-D-glucos-5-enopyranoside 
• 214068-41-4 (1R,2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-2,6-bis-benzyloxymethoxy-cyclohexane-1,3-diol 
• 1053738-99-0 Phosphoric acid benzyl ester (1R,2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-hydroxy-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 1054657-08-7 Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 214068-44-7 Phosphoric acid dibenzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester 
• 1054640-00-4 Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 214068-39-0 (1S,2S,3S,4S,5R,6S)-3,4-Bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexanol 
• 214332-45-3 Acetic acid (1S,2R,3R,4S,5S,6R)-3,4-bis-benzyloxy-2,6-dihydroxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 1184705-54-1 methyl 3,4-di-O-benzyl-6-deoxy-6-iodo-2-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 1184705-86-9 (3R,4S,5S,6S)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene 
• 1184705-55-2 (3R,4S,5S,6R)-6-(benzylamino)-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene 
• 1184705-58-5 (3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene 

Relevant academic research and scientific papers

Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis

A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.

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.