5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Base Information

Chemical Name:5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester
CAS No.:125049-99-2
Molecular Formula:C₂₂H₃₃NO₇
Molecular Weight:423.507
Hs Code.:

Synonyms:5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

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Chemical Property of 5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

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Technology Process of 5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

There total 7 articles about 5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl 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: 67.0%

: 125049-97-0
α-carbo-tert-butoxy-α-carbobenzoxy-δ-O-(tert-butyldimethylsilyl)hydroxynorvaline tert-butyl ester

: 125049-99-2
5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

: 125049-98-1
α-N-carbo-tert-butoxy-α-N-carbobenzoxy-δ-hydroxy-D-norvaline tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1021/jo00293a010

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 125049-99-2
5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

2: 1N NaOH / methanol / 1 h / Ambient temperature

3: Et₃N / tetrahydrofuran / 0.75 h / -20 °C

4: 87 percent / NaBH₄ / tetrahydrofuran; H₂O / 3 h / Ambient temperature

5: 98 percent / imidazole / dimethylformamide / Ambient temperature; further bases used

6: 93 percent / DMAP / acetonitrile / 24 h / Ambient temperature

7: 26 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00293a010

Reference yield:

: 125049-96-9
tert-butyl ester of α-N-carbobenzoxy-δ-O-(tert-butyldimethylsilyl)-D-hydroxynorvaline

: 125049-99-2
5-Benzyloxycarbonyloxy-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / DMAP / acetonitrile / 24 h / Ambient temperature

2: 26 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile;
DOI:10.1021/jo00293a010