(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

Base Information

Chemical Name:(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester
CAS No.:677738-23-7
Molecular Formula:C₂₃H₃₆N₂O₅
Molecular Weight:420.549
Hs Code.:

Synonyms:(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

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Chemical Property of (7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

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Technology Process of (7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

There total 6 articles about (7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl 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: 68.0%

: 677738-22-6
(7S,6R)-[7-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-8-methyl-non-4-enyl]-carbamic acid benzyl ester

: 677738-23-7
(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol0499147

Reference yield:

: 677738-16-8
(8S)-8-tert-butoxycarbonylamino-9-methyl-7-oxo-dec-5-enoic acid methyl ester

: 677738-23-7
(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / NaBH₄ / methanol / 0 °C

2: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: aq. LiOH / tetrahydrofuran / 1 h / 25 °C

4: diphenyl phosphorazidate; Et₃N / toluene / 1 h / Heating

5: 845 mg / toluene / 12 h / Heating

6: 68 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 4: Curtius rearrangement;
DOI:10.1021/ol0499147

Reference yield:

: 677738-17-9
(8S,7R)-8-tert-butoxycarbonylamino-7-hydroxy-9-methyI-dec-5-enoic acid methyl ester

: 677738-23-7
(7S,6R)-(7-tert-butoxycarbonylamino-6-hydroxy-8-methyl-non-4-enyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: aq. LiOH / tetrahydrofuran / 1 h / 25 °C

3: diphenyl phosphorazidate; Et₃N / toluene / 1 h / Heating

4: 845 mg / toluene / 12 h / Heating

5: 68 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; lithium hydroxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 3: Curtius rearrangement;
DOI:10.1021/ol0499147