109536-52-9

Upstream product

• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 824-94-2 p-methoxybenzyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 105-13-5 4-Methoxybenzyl alcohol 
• 69940-02-9 3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 154799-94-7 3-O-(4-Methoxybenzyl)-1,2-O-isopropylidene-4-formylerythrofuranose 
• 69940-04-1 (R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 
• 329899-60-7 (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 69940-04-1 1-[(3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol 
• 82529-87-1 (3aR,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 

Downstream Products

• 107207-31-8 (2R,3R)-2,4-isopropylidenedioxy-3-(4-methoxybenzyloxy)butanol 
• 113643-38-2 (2R,3R)-2,4-isopropylidenedioxy-3-(4-methoxybenzyloxy)butanal 
• 107207-30-7 (4R,5R)-4-Benzyloxymethyl-5-(4-methoxy-benzyloxy)-2,2-dimethyl-[1,3]dioxane 
• 113981-32-1 (4R,5R)-1-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-4,6-isopropylidenedioxy-5-(4-methoxybenzyloxy)hexan-1-one 
• 113643-42-8 (R)-3-<(2R,5S)-5-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-yl>-2-methoxy-5-methyltetrahydrofuran-2-yl>-3-(4-methoxybenzyloxy)prop-1-yne 
• 113643-41-7 (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5,7-isopropylidenedioxy-6-(4-methoxybenzyloxy)heptan-2-ol 
• 113656-57-8 (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol 
• 113643-43-9 (3R,4S)-4-{(2S,3S,5R)-6-[(R)-3-[(S)-5-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-methoxy-5-methyl-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxy)-prop-1-ynyl]-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-hexan-3-ol 
• 126365-86-4 (1R,5R,7S)-1-[(S)-5-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-methoxy-5-methyl-tetrahydro-furan-2-yl]-7-((4S,5S,6R)-5,6-diethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-1-(4-methoxy-benzyloxy)-5-methyl-oct-2-yn-4-ol 
• 113643-44-0 (R)-1-<(3R,5R,6S)-6-<(1R,2R)-2-acetoxy-1-ethylbutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-3-<(5S)-5-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-2-methoxy-5-methyltetrahydrofuran-2-yl>-3-(4-methoxybenzyloxy)prop-1-yne 
• 113643-45-1 (1Z,3R)-1-<(3R,5R,6S)-6-<(1R,2R)-2-acetoxy-1-ethylbutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-3-<(5S)-5-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-2-methoxy-5-methyltetrahydrofuran-2-yl>-3-(4-methoxybenzyloxy)prop-1-ene 
• 113656-58-9 (1R,5R,7S,8S,9S,10R)-1-<(2RS,5S)-5-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-2-methoxy-5-methyltetrahydrofuran-2-yl>-9-ethyl-8,10-isopropylidenedioxy-1-(4-methoxybenzyloxy)-5,7-dimethyldodec-2-yn-4-one 
• 120269-74-1 (2R,3R,6S)-6-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxy)-heptane-1,3,6-triol 
• 115693-80-6 methyl 5-deoxy-3-O-(p-methoxybenzyl)-α-D-ribofuranoside 

Relevant academic research and scientific papers

The Total Synthesis of (-)-Litsenolides C-1 and C-2

The total synthesis of (-)-litsenolides C1 and C2 from D-glucose in 12percent overall yield is described in which the α-alkylidene double-bond is formed by a Wittig reaction of a C-2 oxocarbohydrate derivative.

STEREOSELECTIVE SYNTHESIS OF THE MIDDLE (C10-C17) AND RIGHT (C18-C30) SEGMENTS, AND THEIR COUPLING TO COMPLETE A FORMAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN

The middle (C10-C17) and right (C18-C30) segments of the polyether antibiotic salinomycin were stereoselectively synthesized from D-glucose, D-mannitol, and ethyl L-lactate.Coupling of the two segments followed by construction of the bisketal ring system gave the C10-C30 segment, which was already converted to salinomycin by Kishy.

The Total Synthesis of Litsenolides C1 and C2

Naturally occurring α-alkylidene-γ-butyrolactones can be prepared from a carbohydrate precursor using Wittig methodology to form the exocyclic double bond.