82206-48-2

Upstream product

• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 74-95-3 1,1-dibromomethane 
• 67-68-5 dimethyl sulfoxide 
• 15205-66-0 2-(methylsulfonyl)ethyl alcohol 
• 1243310-65-7 methyl 2,3,6-tri-O-benzyl-4-O-methylthiomethyl-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1243310-56-6 2-(methylsulfonyl)ethoxymethyl acetate 

Downstream Products

• 50256-48-9 methyl 4,6-O-methylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis

The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside.

A new and more efficient synthesis of methylene acetals

A new and efficient synthesis of benzyl chlorides and methylene acetals by use of 2,4-dichloro-6-methoxy[l,3,5]triazine (MeOTCT) and dimethyl sulfoxide has been developed. Chlorides are the major products for benzyl alcohols, while methylene acetals are the major products for secondary alcohols. This procedure provides the highest yields so far for methylene acetals of steroids. A plausible mechanism is proposed on the basis of the experiments. Georg Thieme Verlag Stuttgart.