495378-99-9

Upstream product

• 111727-15-2 (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 1616487-09-2 4-methoxybenzyl N-allyl thiocarbamate 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 495379-01-6 methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-6-O-triflyl-α-D-glucopyranoside 
• 495379-08-3 methyl 2,3-di-O-benzyl-6-deoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-glucopyranoside 
• 495379-25-4 (2S,3R,4S,4aR,5aR,8aR)-3,4-dibenzyloxy-1,5-dioxa-2-methoxy-7a-azacyclobuta[b]decalin-7-one 
• 90633-95-7 methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside 

Relevant academic research and scientific papers

Simple and efficient method for the protection of hydroxyl groups as 4-methoxybenzyl ethers

PMB ethers of alcohols are obtained in good yields and under mild conditions using the 4-methoxybenzyl N-allyl thiocarbamate and N-bromosuccinimide (NBS)/TfOH as the catalyst. The present method is very fast, simple, and efficient. Copyright

Stereocontrolled formation of oxacephams from carbohydrates

The [2+2] cycloaddition of chlorosulfonyl isocyanate to (Z)-4-O-propenyl ethers 16, 17, 29 and 30 proceeds with an excellent stereoselectivity in the case of ether 16 and with moderate stereoselectivity in remaining cases. Adducts were transformed into corresponding oxacephams: 37 in the first case, a mixture of 37/40 in the second and third case, and a mixture of 50/51 in the last case. In all instances addition to the si-re side of the olefin dominates. Oxacephams 41 and 52 with opposite R-configuration at the bridgehead carbon C-5a can be obtained by the alternate methodology based on the alkylation of nitrogen in 4-vinyloxyazetidin-2-one by protected 6-O-triflate 24 or 25, followed by cyclization via intramolecular displacement of the vinyloxy group. Compounds 37, 40, 41, 50, 51 and 52 constitute a convenient entry leading to polyfunctionalized oxacephams.