(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

Base Information

Chemical Name:(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone
CAS No.:302605-67-0
Molecular Formula:C₃₂H₂₈O₇
Molecular Weight:524.57
Hs Code.:

Synonyms:(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

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Chemical Property of (3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

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Technology Process of (3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

There total 6 articles about (3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone 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: 46.0%

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

: 302605-68-1
(3R,4R)-3-hydroxy-5-trityloxy-4-pentanolide

: 302605-67-0
(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

: 302605-79-4
(3R,4R,5R)-3-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-4-hydroxy-5-trityloxymethyl-dihydro-furan-2-one

Guidance literature:: (3R,4R)-3-hydroxy-5-trityloxy-4-pentanolide; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -75 ℃; for 0.5h;

piperonal; In tetrahydrofuran; at -75 ℃; for 0.5h;
DOI:10.1271/bbb.64.1563

Reference yield:

: 58-86-6
D-xylose

: 302605-67-0
(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 48 percent / 4-(dimethylamino)pyridine / pyridine / 2 h / 60 °C

2.1: 85 percent / NaHCO₃; Br₂ / ethanol; H₂O / 16 h / 20 °C

3.1: 87 percent / 4-(dimethylamino)pyridine / acetonitrile / 1 h / -10 °C

4.1: 84 percent / tributyltin hydride; 2,2'-azobisisobutyronitrile / benzene / 1 h / Heating

5.1: diisopropylamine; n-BuLi / tetrahydrofuran / 0.5 h / -75 °C

5.2: 46 percent / tetrahydrofuran / 0.5 h / -75 °C

With dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; diisopropylamine; In tetrahydrofuran; pyridine; ethanol; water; acetonitrile; benzene; 1.1: Cyclocondensation / 2.1: Oxidation / 3.1: Condensation / 4.1: Reduction / 5.1: Metallation / 5.2: Addition;
DOI:10.1271/bbb.64.1563

Reference yield:

: 55726-00-6,72521-12-1,72521-13-2,72521-20-1,72521-21-2,72521-22-3,131285-09-1,131285-24-0
(3R,4R,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol

: 302605-67-0
(3R,4R,5R)-4-hydroxy-3-[(1S)-1-hydroxy-1-(3,4-methylenedioxyphenyl)methyl]-5-trityloxymethyldihydro-2(3H)-furanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / NaHCO₃; Br₂ / ethanol; H₂O / 16 h / 20 °C

2.1: 87 percent / 4-(dimethylamino)pyridine / acetonitrile / 1 h / -10 °C

3.1: 84 percent / tributyltin hydride; 2,2'-azobisisobutyronitrile / benzene / 1 h / Heating

4.1: diisopropylamine; n-BuLi / tetrahydrofuran / 0.5 h / -75 °C

4.2: 46 percent / tetrahydrofuran / 0.5 h / -75 °C

With dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; diisopropylamine; In tetrahydrofuran; ethanol; water; acetonitrile; benzene; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Metallation / 4.2: Addition;
DOI:10.1271/bbb.64.1563