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

Base Information

• Chemical Name: 3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate
• CAS No.: 181772-74-7
• Molecular Formula: C₃₄H₅₀N₂O₅
• Molecular Weight: 566.781
• Mol file: 181772-74-7.mol

Synonyms:3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate

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

There total 10 articles about 3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-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: 85.0%

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + 3''-pentyl (R,E)-4-[2,2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]but-2-enoate (181772-66-7) → 3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate (181772-74-7)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

3''-pentyl (R,E)-4-[2,2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]but-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2010.10.067

Reference yield: 85.0%

lithium benzyl-(R)-1-phenylethylamide + 3''-pentyl (R,E)-4-[2,2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]but-2-enoate (181772-66-7) → 3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate (181772-74-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/0957-4166(96)00230-3

Reference yield:

ethyl (3R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoate (181772-51-0) → 3''-pentyl (R,R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-[2',2';-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate (181772-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / CSA / acetone

2: 97 percent / sodium bis(2-methoxyethoxy)aluminium hydride

3: 1.) oxalyl chloride, DMSO, 2.) iPr₂NEt

4: toluene / 60 °C

5: 85 percent / tetrahydrofuran / -78 °C

With oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; acetone; toluene;

DOI:10.1016/0957-4166(96)00230-3

upstream raw materials:

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

ethyl (3R)-4-(tert-butyloxycarbonyl)amino-3-hydroxybutanoate

(R)-2-[2',2'-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]ethanol

(R)-2-[2',2'-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]ethanal

Downstream raw materials:

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

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