N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

Base Information

• Chemical Name: N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester
• CAS No.: 95319-02-1
• Molecular Formula: C₁₉H₂₉NO₅
• Molecular Weight: 351.443
• Mol file: 95319-02-1.mol

Synonyms:N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

Chemical Property of N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

There total 5 articles about N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester 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: 97.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + BOC-O-benzyl-L-serine (23680-31-1) → N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester (95319-02-1)

Guidance literature:

tert-Butyl 2,2,2-trichloroacetimidate; BOC-O-benzyl-L-serine; With boron trifluoride diethyl etherate; In dichloromethane; cyclohexane; at 20 ℃; for 1h;

With sodium hydrogencarbonate; for 0.0833333h;

DOI:10.1002/chem.201801029

Reference yield: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + BOC-O-benzyl-L-serine (23680-31-1) → N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester (95319-02-1)

Guidance literature:

With dmap; In tert-butyl alcohol; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(01)00900-0

Reference yield: 64.0%

methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate (80963-10-6) + tert-butyl alcohol (75-65-0) → N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester (95319-02-1)

Guidance literature:

With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)]; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 24h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201602801

upstream raw materials:

BOC-O-benzyl-L-serine

tert-Butyl 2,2,2-trichloroacetimidate

di-tert-butyl dicarbonate

Benzyloxymethyl chloride

Downstream raw materials:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester