610302-79-9

Upstream product

• 109-80-8 1.3-propanedithiol 
• 610302-77-7 [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-tosyloxyethyl)tetrahydropyran 
• 85593-49-3 1,6-anhydro-2,3,4-trideoxy-2,4-di-C-methyl-β-D-ribo-hexopyranoside 
• 128790-96-5 Methanesulfonic acid (1S,2R,3S,4R,5R)-2-methyl-4-phenylsulfanylmethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester 
• 76690-23-8 (1S,2S,3S,4R,5R)-2,4-Dimethyl-6,8-dioxabicyclo<3.2.1>octan-3-ol 
• 610302-57-3 (2R,3R,5S,6S)-2-methoxy-3,5-dimethyl-6-(hydroxymethyl)tetrahydropyran 
• 610302-75-5 [2R,3R,5S,6S,6(1R)]-2-methoxy-3,5-dimethyl-6-(1-hydroxyethyl)tetrahydropyran 
• 100757-48-0 1,6-anhydro-2,4-dideoxy-4-methyl-2-(phenylthiomethyl)-β-D-glucopyranose 

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.