3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate

Base Information

• Chemical Name: 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate
• CAS No.: 1262515-94-5
• Molecular Formula: C₂₇H₄₂N₂O₇
• Molecular Weight: 506.64
• Mol file: 1262515-94-5.mol

Synonyms:3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate

Chemical Property of 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate

There total 11 articles about 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate 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: 82.0%

3'-pentyl (R,R)-3-amino-4-[2',2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate (1262515-93-4) + benzyl chloroformate (501-53-1,94274-21-2) → 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate (1262515-94-5)

Guidance literature:

With sodium hydrogencarbonate; sodium chloride; In dichloromethane; chloroform; water; at 20 ℃; for 0.75h;

DOI:10.1016/j.tet.2010.10.067

Reference yield:

bromoacetic acid,3-pentyl ester (59956-49-9) → 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate (1262515-94-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: benzene / 16 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / ethanol; water; toluene

3.1: toluene / 4 h / 70 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 °C / Inert atmosphere

5.1: 20 % Pd(OH)2/C; hydrogen; acetic acid / methanol / 20 h / 4560.31 Torr

6.1: sodium hydrogencarbonate; sodium chloride / dichloromethane; chloroform; water / 0.75 h / 20 °C

With n-butyllithium; 20 % Pd(OH)2/C; hydrogen; sodium hydrogencarbonate; acetic acid; sodium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; toluene; benzene; 3.1: Wittig reaction;

DOI:10.1016/j.tet.2010.10.067

Reference yield:

ethyl (3R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoate (181772-51-0) → 3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate (1262515-94-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (R)-10-camphorsulfonic acid / acetone / 2 h / 70 °C / Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -63 °C / Inert atmosphere

3.2: -63 - 20 °C / Inert atmosphere

4.1: toluene / 4 h / 70 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: 20 % Pd(OH)2/C; hydrogen; acetic acid / methanol / 20 h / 4560.31 Torr

7.1: sodium hydrogencarbonate; sodium chloride / dichloromethane; chloroform; water / 0.75 h / 20 °C

With n-butyllithium; oxalyl dichloride; 20 % Pd(OH)2/C; (R)-10-camphorsulfonic acid; hydrogen; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; acetone; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Wittig reaction;

DOI:10.1016/j.tet.2010.10.067

upstream raw materials:

[2-oxo-2-(3'-pentyloxy)ethyl]triphenylphosphonium bromide

3'-pentyl (R,R)-3-amino-4-[2',2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate

benzyl chloroformate

2-pentanol

Downstream raw materials:

C₁₅H₂₂N₂O₅*ClH

methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-5-hydroxy-6-[N-(2',4'-hexadienoyl)amino]hexanoate

methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-4-[2',2'-dimethyl-N(3')-(2,4-hexadienoyl)-1',3'-oxazolidin-5'-yl]butanoate

(R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid