(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

Base Information

Chemical Name:(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide
CAS No.:326606-33-1
Molecular Formula:C₃₂H₂₈O₇
Molecular Weight:524.57
Hs Code.:

Synonyms:(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

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Chemical Property of (2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

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Technology Process of (2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

There total 6 articles about (2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

: 120-57-0,30024-74-9
piperonal

: 326606-31-9
(3R,4S)-3-hydroxy-5-trityloxy-4-pentanolide

: (3S,4R,5S)-3-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-hydroxy-5-trityloxymethyl-dihydro-furan-2-one

: 326606-33-1
(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

Guidance literature:: (3R,4S)-3-hydroxy-5-trityloxy-4-pentanolide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -75 ℃; for 0.25h;

piperonal; In tetrahydrofuran; hexane; at -75 ℃; for 1h;
DOI:10.1271/bbb.64.2320

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
L-arabinose

: 326606-33-1
(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 67 percent / 4-dimethylaminopyridine; pyridine / 1 h / 60 °C

2.1: 87 percent / bromine; NaHCO₃ / H₂O; ethanol / 16 h / 20 °C

3.1: 86 percent / 4-dimethylaminopyridine; pyridine / acetonitrile / 1 h / 0 °C

4.1: 92 percent / tri-n-butyltin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 1 h / Heating

5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.25 h / -75 °C

5.2: 56 percent / tetrahydrofuran; hexane / 1 h / -75 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; water; acetonitrile; benzene; 5.2: aldol condensation;
DOI:10.1271/bbb.64.2320

Reference yield:

: 76-83-5
trityl chloride

: 326606-33-1
(2R,3R,4S)-3-hydroxy-2-[(1R)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxy-4-pentanolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 67 percent / 4-dimethylaminopyridine; pyridine / 1 h / 60 °C

2.1: 87 percent / bromine; NaHCO₃ / H₂O; ethanol / 16 h / 20 °C

3.1: 86 percent / 4-dimethylaminopyridine; pyridine / acetonitrile / 1 h / 0 °C

4.1: 92 percent / tri-n-butyltin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 1 h / Heating

5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.25 h / -75 °C

5.2: 56 percent / tetrahydrofuran; hexane / 1 h / -75 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; water; acetonitrile; benzene; 5.2: aldol condensation;
DOI:10.1271/bbb.64.2320