183170-36-7

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 162583-82-6 (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 162583-81-5 methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 
• 162680-20-8 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 299199-12-5 methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 18929-63-0 methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside 
• 342789-73-5 methyl 3,4-di-O-(4-methoxybenzyl)-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside 
• 342789-72-4 methyl 3,4-di-O-(4-methoxybenzyl)-α-D-glucopyranoside 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 162583-79-1 methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 26927-44-6 methyl 2,6-di-O-benzoyl-α-D-glycopyranoside 

Downstream Products

• 162583-83-7 methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5) 
• 162583-79-1 methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 183170-43-6 (1R,2S,3S,4R,5S)-2-Benzyloxy-5-hydroxymethyl-3,4-bis-(4-methoxy-benzyloxy)-cyclopentanol 
• 183170-55-0 Phosphoric acid dibenzyl ester (1R,2S,3R,4S,5R)-2,3-bis-benzyloxy-5-(bis-benzyloxy-phosphoryloxy)-4-(bis-benzyloxy-phosphoryloxymethyl)-cyclopentyl ester 
• 221690-39-7 Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S)-2-benzyloxy-5-benzyloxymethyl-3,4-bis-(bis-benzyloxy-phosphoryloxy)-cyclopentyl ester 
• 183170-47-0 (1R,2S,3S,4R,5S)-2-Benzyloxy-5-benzyloxymethyl-3,4-bis-(4-methoxy-benzyloxy)-cyclopentanol 
• 183170-45-8 [(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol 
• 1053735-44-6 (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde 
• 183170-49-2 (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane 
• 183170-53-8 (1R,2S,3S,4R,5R)-3-Benzyloxy-5-benzyloxymethyl-cyclopentane-1,2,4-triol 
• 183170-51-6 (1R,2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-cyclopentane-1,2-diol 
• 221690-29-5 (1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-1,2-bis-<(p-methoxybenzyl)oxy>-5-vinylcyclopentane 
• 162583-84-8 (1R,2S,3S,4R,5R)-3-(benzyloxy)-1,2,4-trihydroxy-5-vinylcyclopentane 
• 173911-76-7 methyl (Z)-2-O-benzyl-3,4-di-O-(p-methoxybenzyl)-6-O-acetyl-α-D-glucos-5-enopyranoside 

Relevant academic research and scientific papers

Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers

The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.

Chiral cyclopentane-based mimics of D-myo-inositol 1,4,5-trisphosphate from D-glucose

Two routes from D-glucose to chiral, ring-contracted analogs of the second messenger D-myo-inositol 1,4,5-trisphosphate are described. Methyl α-D-glucopyranoside was converted by an improved procedure into methyl 4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (6) and thence into methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5) (14) in four steps. In the first ring-contraction method 14 was converted into methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-e nopyranoside (1,5) (15), which on sequential treatment with Cp2Zr(n-Bu)2 followed by BF3·Et2O afforded a mixture of (1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-1,2-bis[(p-methoxybenzyl)oxy] -5-vinylcyclopentane (16) and its 4S,5R diastereoisomer 17. Removal of the p-methoxybenzyl groups of 16 and subsequent phosphorylation and deprotection afforded the first target compound, (1R,2R,3S,4R,5S)-3-hydroxy-1,2,4-tris(phosphonooxy)-5-vinylcyclopentan e (3). In the second route, intermediate 14 was subjected to SmI2-mediated ring contraction to give (1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-5-(hydroxymethyl)-1,2-bis[(p- methoxybenzyl)oxy]cyclopentane (20). Benzylation of 20 provided (1R,2S,3S,4R,5S)-3-(benzyloxy)-6-[(benzyloxy)methyl]-4-hydroxy-1,2-bis [(p-methoxybenzyl)oxy]cyclopentane (22) and (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-(hydroxymethyl)-1,2-bis[(p-metho xybenzyl)oxy]cyclopentane (21), which were elaborated to the target trisphosphates (1R,2R,3S,4R,5S)-3-hydroxy-5-(hydroxymethyl)-1,2,4-tris(phosphonooxy)c yclopentane (4) and (1R,2S,3R,4R,5S)-1,2-dihydroxy-3,4-bis(phosphonooxy)-5-[(phosphonooxy) methyl]cyclopentane (5), respectively. Both 3 and 4 mobilized intracellular Ca2+, but 4 was only a few fold less potent than D-myo-inositol 1,4,5-trisphosphate, demonstrating that effective mimics can be designed that do not bear a six-membered ring.