(3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine

Base Information

• Chemical Name: (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine
• CAS No.: 858930-18-4
• Molecular Formula: C₂₆H₃₇NO₄Si
• Molecular Weight: 455.67
• Mol file: 858930-18-4.mol

Synonyms:(3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine

Chemical Property of (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine

There total 1 articles about (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine 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: 71.0%

tert-butylchlorodiphenylsilane (58479-61-1) + tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate (635319-09-4) → (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine (858930-18-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1021/jm050269z

Reference yield: 97.0%

(3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine (858930-18-4) + bromethyl methyl ether (13057-17-5) → (3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-methoxymethoxypyrrolidine (858930-19-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 70 ℃; for 3h;

DOI:10.1021/jm050269z

Reference yield:

(3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxypyrrolidine (858930-18-4) → (3R,4R)-4-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxypyrrolidine (858930-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / diisopropylethylamine / toluene / 3 h / 70 °C

2: 65 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3: 88 percent / sodium hydride / dimethylformamide / 1 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm050269z

upstream raw materials:

tert-butylchlorodiphenylsilane

tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate

Downstream raw materials:

(3R,4R)-1-tert-butoxycarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-3-methoxymethoxypyrrolidine

(3R,4R)-4-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxypyrrolidine