113918-87-9

Upstream product

• 18427-19-5 1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 58399-55-6 3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 113918-88-0 1-[(3aR,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol 
• 113918-88-0 (R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}ethane-1,2-diol 
• 108470-18-4 3-C-(2-benzyloxyethyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-methyl-β-L-talofuranose 
• 96181-79-2 5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(S)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-(R)-methyl-tetrahydropyran 
• 108470-17-3 3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-methylene-α-D-ribo-hexofuranose 
• 108470-19-5 (2R,3R,4S)-2-C-(2-benzyloxyethyl)-3-formyloxy-5-(4-methoxybenzyloxy)-4-methylpentanal 
• 96181-86-1 (2S,5S,6S)-2-benzyloxyethyl-5,6-dihydro-2-isopropyloxy-6-<2-(4-methoxybenzyloxy)-1(S)-methylethyl>-3-methyl-2H-pyran 
• 96243-61-7 5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(S)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-(S)-methyl-tetrahydropyran 
• 96181-78-1 5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran 
• 113918-91-5 3-C-(2-benzyloxyethyl)-3,5-dideoxy-1,2-O-isopropylidene-5-methylene-α-D-ribo-hexofuranose 
• 113918-95-9 (2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol 
• 113918-89-1 (R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol 
• 113918-98-2 (2S,5S,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-ol 
• 113918-93-7 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose 

Relevant academic research and scientific papers

Intramolecular aldol condensation applied to D-glucose-derived δ-ketoaldehydes: Access to enantiomerically pure six-membered carbocycles

An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further

Formal synthesis of salinosporamide a starting from D-glucose

A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from D-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of g-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey's intermediate of salinosporamide A. Georg Thieme Verlag Stuttgart.

TOTAL SYNTHESIS OF TYLONOLIDE, THE AGLYCONE OF THE 16-MEMBERED RING MACROLIDE TYLOSIN, FROM D-GLUCOSE. SELECTIVE APPLICATION OF MPM AND DMPM PROTECTING GROUPS FOR HYDROXY FUNCTIONS

Segments i (C11-C17) and ii (C1-C10), synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protecting groups, were esterified and cyclized to the 16-membered enone , which was readily converted to tylonolide, the aglycone