222545-13-3

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 199918-03-1 methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside 

Downstream Products

• 1225450-91-8 C₂₃H₂₈O₉ 
• 922733-50-4 methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside 
• 1404060-71-4 methyl 4-O-(2,3-anhydro-4,6-di-O-acetyl-α-D-mannopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside 
• 1404060-73-6 methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-iodo-α-D-galactopyranoside 
• 1404060-74-7 methyl 2,3-di-O-p-methoxybenzyl-4-acetylthio-6-deoxy-α-D-glucopyranoside 
• 1404060-76-9 methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-thio-α-D-glucopyranoside 
• 1404060-78-1 methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-glucopyranoside 
• 1404060-82-7 methyl 2,3-di-O-p-methoxybenzyl-4-acetylthio-6-deoxy-α-D-galactopyranoside 
• 1404060-83-8 methyl 2,3-di-O-p-methoxybenzyl-6-deoxy-4-thio-α-D-galactopyranoside 
• 1404060-84-9 methyl 4-S-(2,3-anhydro-4,6-di-O-acetyl-α-D-allopyranosyl)-2,3-di-O-p-methoxybenzyl-6-deoxy-α-D-galactopyranoside 
• 186541-50-4 (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol 
• 134407-60-6 methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside 
• 222545-23-5 (1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane 

Relevant academic research and scientific papers

Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates

Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona

Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose

The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

Synthesis of a photoaffinity analogue of phosphatidylinositol 3,4-bisphosphate, an effector in the phosphoinositide 3-kinase signaling pathway

A Ferrier rearrangement strategy starting from α-D-glucose gave a protected inositol, which after coupling to a chiral diacylglycerol phosphoramidite, provided a tritium-labeled, benzophenone-containing derivative of P-1-(O-aminopropyl) linked dipalmitoyl PtdIns(3,4)P2. Copyright (C) 1996 Elsevier Science Ltd.