(2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

Base Information

• Chemical Name: (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine
• CAS No.: 774611-13-1
• Molecular Formula: C₄₆H₅₅NO₅Si
• Molecular Weight: 730.032
• Mol file: 774611-13-1.mol

Synonyms:(2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

Chemical Property of (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

There total 10 articles about (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine 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: 96.9%

(2R,3S,4R)-2-[(1R)-1-hydroxy-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine (774611-12-0) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine (774611-13-1)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 65 ℃; for 72h;

DOI:10.1071/CH04009

Reference yield:

(2R,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-vinyl-oxirane → (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine (774611-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / LiOTf / 1 h / 110 °C / microwave irradiation

2: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 77 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

4: K₂OsO₄*2H₂O; N-methylmorpholine oxide; pyridine / acetone; H₂O / 168 h / 20 °C

5: 100 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

6: 83.7 percent / NaOH / methanol; H₂O / 2 h / 110 °C / microwave irradiation

7: 96.9 percent / imidazole / acetonitrile / 72 h / 65 °C

With pyridine; 1H-imidazole; sodium hydroxide; potassium osmate(VI); Grubbs catalyst first generation; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1071/CH04009

Reference yield:

7-[(4-methoxyphenyl)methoxy]-(4R)-hydroxy-(3S)-allylaminohept-1-ene (476171-47-8) → (2R,3S,4S)-2-[(1R)-1-[[(1,1-dimethylethyl)(diphenyl)silyl]oxy]-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine (774611-13-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 77 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

3: K₂OsO₄*2H₂O; N-methylmorpholine oxide; pyridine / acetone; H₂O / 168 h / 20 °C

4: 100 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

5: 83.7 percent / NaOH / methanol; H₂O / 2 h / 110 °C / microwave irradiation

6: 96.9 percent / imidazole / acetonitrile / 72 h / 65 °C

With pyridine; 1H-imidazole; sodium hydroxide; potassium osmate(VI); Grubbs catalyst first generation; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1071/CH04009

upstream raw materials:

(2R,3S,4R)-2-[(1R)-1-hydroxy-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

tert-butylchlorodiphenylsilane

(1R,6R,7S,7aS)-1-[3-[(4-methoxyphenyl)methoxy]propyl]-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

(1R,6R,7S,7aR)-tetrahydro-1-[3-[(4-methoxyphenyl)methoxy]propyl]-6,7-bis(phenylmethoxy)-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Downstream raw materials:

(1S,2R,8R,8aS)-octahydro-1,2-bis(phenylmethoxy)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-indolizine

(1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine

(R)-4-((2S,3S,4R)-3,4-Bis-benzyloxy-pyrrolidin-2-yl)-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol