allyl N-(benzyloxycarbonyl)-O--L-threoninate

Base Information

• Chemical Name: allyl N-(benzyloxycarbonyl)-O--L-threoninate
• CAS No.: 117710-13-1
• Molecular Formula: C₃₁H₄₀N₂O₉
• Molecular Weight: 584.667
• Mol file: 117710-13-1.mol

Synonyms:allyl N-(benzyloxycarbonyl)-O--L-threoninate

Chemical Property of allyl N-(benzyloxycarbonyl)-O--L-threoninate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of allyl N-(benzyloxycarbonyl)-O--L-threoninate

There total 3 articles about allyl N-(benzyloxycarbonyl)-O--L-threoninate 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: 98.0%

allyl N-(benzyloxycarbonyl)-L-threoninate (117710-12-0) + (S)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-methoxyphenyl)propanoic acid (73584-84-6) → allyl N-(benzyloxycarbonyl)-O--L-threoninate (117710-13-1)

Guidance literature:

With dmap; Isopropenyl chloroformate; triethylamine; In dichloromethane; at -5 ℃; for 0.5h;

DOI:10.1021/jo00264a022

Reference yield:

N-[(phenylmethoxy)carbonyl]-L-threonine (19728-63-3) → allyl N-(benzyloxycarbonyl)-O--L-threoninate (117710-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Cs₂CO₃ / dimethylformamide / 2 h

2: 98 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.5 h / -5 °C

With dmap; Isopropenyl chloroformate; caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00264a022

Reference yield:

methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-N,O-dimethyl-L-tyrosinate (117710-21-1) → allyl N-(benzyloxycarbonyl)-O--L-threoninate (117710-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / 2 N NaOH / methanol / 0 - 5 °C

2: 98 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.5 h / -5 °C

With dmap; sodium hydroxide; Isopropenyl chloroformate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00264a022

upstream raw materials:

allyl N-(benzyloxycarbonyl)-L-threoninate

(S)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-methoxyphenyl)propanoic acid

N-[(phenylmethoxy)carbonyl]-L-threonine

methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-N,O-dimethyl-L-tyrosinate

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-[(S)-3-(4-methoxy-phenyl)-2-methylamino-propionyloxy]-butyric acid allyl ester; compound with trifluoro-acetic acid