(2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole

Base Information

• Chemical Name: (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole
• CAS No.: 476171-50-3
• Molecular Formula: C₂₈H₃₇NO₅
• Molecular Weight: 467.605
• Mol file: 476171-50-3.mol

Synonyms:(2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole

Chemical Property of (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole

There total 11 articles about (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole 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: 74.2%

benzyl bromide (100-39-0) + (2S)-((1'R)-hydroxy-4'-[(4-methoxyphenyl)methoxy]butyl)-N-tert-butyloxycarbonyl-2,5-dihydropyrrole (476171-49-0) → (1R,7aS)-1-[3-[(4-methoxyphenyl)methoxy]propyl]-5,7a-dihydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (774611-07-3) + (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole (476171-50-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1021/jo025977w

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole (476171-50-3)

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: 74.2 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; Grubbs catalyst first generation; n-butyllithium; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; toluene; Petroleum ether; 4.1: Sharpless epoxidation / 5.1: Swern oxidation;

DOI:10.1021/jo025977w

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (2S)-[(1'R)-phenylmethoxy-4'-[(4-methoxyphenyl)methoxy]butyl]-N-tert-butyloxycarbonyl-2,5-dihydropyrrole (476171-50-3)

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: 74.2 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

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

DOI:10.1021/jo025977w

upstream raw materials:

benzyl bromide

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

p-Methoxybenzyl bromide

4-Methoxybenzyl alcohol

Downstream raw materials:

(8R,8aS)-8-benzyloxy-3,5,6,7,8,8a-hexahydroindolizine

(-)-8-benzyloxy-swainsonine

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol