(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

Base Information

Chemical Name:(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid
CAS No.:647008-08-0
Molecular Formula:C₂₃H₂₄O₆
Molecular Weight:396.44
Hs Code.:

Synonyms:(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

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Chemical Property of (2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

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Technology Process of (2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

There total 8 articles about (2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid 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:

: (2S,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-3-isopropyl-5-(4-methoxy-phenyl)-pent-4-ynal

: 647008-08-0
(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 ℃; for 1.5h;
DOI:10.1271/bbb.67.2215

Reference yield:

: 647007-90-7
(2R,3R)-4-methyl-2-(3,4-methylenedioxyphenyl)methyl-1,3-pentanediol

: 647008-08-0
(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 98.3 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 0 - 20 °C

2: 90.8 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

3: 79.7 percent / acetic acid / tetrahydrofuran; H₂O / 16 h / 20 °C

4: tetrahydrofuran / -78 °C

5: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 12 h / 20 °C

6: sodium chlorite; 2-methyl-2-butene; sodium dihydrogen phosphate / H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 °C

With 1H-imidazole; dmap; sodium chlorite; tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Swern oxidation;
DOI:10.1271/bbb.67.2215

Reference yield:

: 647007-85-0
(2R)-1-hydroxy-4-methyl-2-(3,4-methylenedioxyphenyl)methyl-3-pentanone

: 647008-08-0
(2S,3R)-3-hydroxy-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentynoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: tetrahydrofuran / -78 °C

2: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 12 h / 20 °C

3: sodium chlorite; 2-methyl-2-butene; sodium dihydrogen phosphate / H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 °C

With sodium chlorite; tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; 4 A molecular sieve; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1271/bbb.67.2215