128790-96-5

Upstream product

• 100757-48-0 1,6-anhydro-2,4-dideoxy-4-methyl-2-(phenylthiomethyl)-β-D-glucopyranose 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 610302-63-1 (2R,4S,5S,6S)-1-(1,3-dithian-2-yl)-5-hydroxy-2,4-dimethyl-6-tosyloxyheptane 
• 610302-79-9 (2R,4S,5S,6R)-1-(1,3-dithian-2-yl)-5-hydroxy-2,4-dimethyl-6-tosyloxyheptane 
• 610302-61-9 [2S,3R,5S,6S,6(1S)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran 
• 610302-77-7 [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran 

Relevant academic research and scientific papers

Stereoselective preparation of chiral building blocks having 1,3-syn-dimethyl group from D-glucose

Reaction of (2S,3R,5S,6S)-2-methoxy-3,5-dimethyl-tetrahydro-2H-pyran-6-carbaldehyde (α-8) with MeMgCl gave (6′S)-α-9 as a single isomer which was converted into (5S,6R)-epoxide (cis-12) by a sequence of reactions involving tosylation, ring-opening by the reaction with HS(CH2)3SH, and treatment with NaOMe. When α-8 and its β-anomer (β-8) respectively reacted with Me-Ti(Oi-Pr)3 and the resulting alcohols were subjected to similar transformation as above, (5S,6S)-epoxide (trans-12) was obtained irrespective of the anomeric configuration. The reaction of trans-12 with lithium alkynylaluminates 13a and 13b took place at the position 6 to afford the corresponding alkynes 14a and 14b.