2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

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Chemical Name:2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine
CAS No.:476171-55-8
Molecular Formula:C₂₁H₃₃NO₇
Molecular Weight:411.496
Hs Code.:

Synonyms:2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

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Chemical Property of 2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

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Technology Process of 2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

There total 11 articles about 2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine 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: 89.5%

: 476171-49-0
(2S)-((1'R)-hydroxy-4'-[(4-methoxyphenyl)methoxy]butyl)-N-tert-butyloxycarbonyl-2,5-dihydropyrrole

: 476171-55-8
2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

Guidance literature:: With potassium osmate(VI); water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 24h;
DOI:10.1021/jo025977w

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 476171-55-8
2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 0.17 h

1.2: 5.50 g / tetrahydrofuran / 22 h / 20 °C

2.1: N-BuLi / tetrahydrofuran; petroleum ether / 0.17 h

2.2: 86.2 percent / tetrahydrofuran; petroleum ether / 20 h / 20 °C

3.1: 98 percent / REDAL / tetrahydrofuran; toluene / 3.5 h / 20 °C

4.1: D-(-)-diisopropyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 2.5 h / -15 °C

5.1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -50 °C

5.2: triethylamine / CH₂Cl₂ / -50 - 20 °C

6.1: KHMDS / toluene / 0.08 h / 0 °C

6.2: 2.76 g / toluene / 3 h / 0 - 20 °C

7.1: 88.2 percent / p-toluenesulfonic acid monohydrate / 72 h / 105 °C

8.1: 98 percent / triethylamine / tetrahydrofuran / 24 h / 20 °C

9.1: 95.2 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 h / Heating

10.1: 89.5 percent / K₂OsO₄*2H₂O; N-methylmorpholine N-oxide; water / acetone / 24 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium osmate(VI); Grubbs catalyst first generation; n-butyllithium; oxalyl dichloride; water; potassium hexamethylsilazane; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; acetone; toluene; Petroleum ether; 4.1: Sharpless epoxidation / 5.1: Swern oxidation;
DOI:10.1021/jo025977w

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 476171-55-8
2R-(1'R-hydroxy-4'-[(4-methoxyphenyl)methoxy]-butyl)-N-tert-butyloxycarbonyl-3R,4S-dihydroxypyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: HBr; acetic acid / 20 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h

2.2: 5.50 g / tetrahydrofuran / 22 h / 20 °C

3.1: N-BuLi / tetrahydrofuran; petroleum ether / 0.17 h

3.2: 86.2 percent / tetrahydrofuran; petroleum ether / 20 h / 20 °C

4.1: 98 percent / REDAL / tetrahydrofuran; toluene / 3.5 h / 20 °C

5.1: D-(-)-diisopropyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 2.5 h / -15 °C

6.1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -50 °C

6.2: triethylamine / CH₂Cl₂ / -50 - 20 °C

7.1: KHMDS / toluene / 0.08 h / 0 °C

7.2: 2.76 g / toluene / 3 h / 0 - 20 °C

8.1: 88.2 percent / p-toluenesulfonic acid monohydrate / 72 h / 105 °C

9.1: 98 percent / triethylamine / tetrahydrofuran / 24 h / 20 °C

10.1: 95.2 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 h / Heating

11.1: 89.5 percent / K₂OsO₄*2H₂O; N-methylmorpholine N-oxide; water / acetone / 24 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium osmate(VI); Grubbs catalyst first generation; n-butyllithium; oxalyl dichloride; water; hydrogen bromide; potassium hexamethylsilazane; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; acetone; toluene; Petroleum ether; 5.1: Sharpless epoxidation / 6.1: Swern oxidation;
DOI:10.1021/jo025977w