138535-84-9

Upstream product

• 13263-74-6 D-xylose diethyl dithioacetal 
• 100-52-7 benzaldehyde 
• 222408-75-5 2,3-di-O-benzyl-4,5-O-isopropylidene-D-xylose diethyl dithioacetal 
• 138661-13-9 2,4:3,5-di-O-benzylidene-D-xylose diethyl dithioacetal 

Downstream Products

• 222408-76-6 4,5-di-O-benzoyl-2,3-di-O-benzyl-D-xylose diethyl dithioacetal 
• 763110-47-0 2,3-bis(phenylmethyloxy)-5-[(1,1-dimethylethyl)dimethylsilyloxy]-D-xylose 
• 763110-48-1 (3R,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-one 
• 768386-42-1 (2R,3S,4S)-3,4-bis(phenylmethyloxy)-1-[(1,1-dimethylethyl)dimethylsilyloxy]hex-5-en-2-ol 
• 222556-01-6 2,5-anhydro-3,4-di-O-benzyl-D-iditol 
• 222408-81-3 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol 
• 222408-79-9 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol 
• 222408-77-7 5,6-di-O-benzoyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-iditol 

Relevant academic research and scientific papers

Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization

Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

The reduction of benzylidene derivatives of pentose diethyl dithioacetals with lithium aluminium hydride-aluminium trichloride

Di-O-benzylidene derivatives of pentose diethyl dithioacetals were reduced to di-O-benzyl pentose diethyl dithioacetals in high yield.In three of the five cases studied, single products were obtained: 2,3:4,5-di-O-benzylidene-D-arabinose diethyl dithioace