(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

Base Information

Chemical Name:(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione
CAS No.:68691-66-7
Molecular Formula:C₁₉H₁₉BrN₂O₇
Molecular Weight:467.273
Hs Code.:

(5<i>S</i>)-4<i>c</i>-(4-bromo-benzoyloxy)-3<i>c</i>-hydroxy-3<i>t</i>-methyl-12-methylene-(5<i>r</i><i>N</i>,5<i>r</i>'<i>O</i>,8<i>t</i>'<i>O</i>)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

Synonyms:(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

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Chemical Property of (5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

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Technology Process of (5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

There total 9 articles about (5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione 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: 33.0%

: 68691-65-6
(3S,4S,5S,8R)-3,4-Dihydroxy-3-methyl-12-methylene-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

: 586-75-4
4-chlorobenzoyl chloride

: 68691-66-7
(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; for 4h; Ambient temperature;
DOI:10.1021/jm9708386

Reference yield:

: 63777-16-2
dihydrobicyclomycin 2',3'-acetonide

: 68691-66-7
(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran / 0.25 h / Ambient temperature

2: aq. NaOH / propan-2-ol / 0.33 h / Ambient temperature

3: 67 percent / aq. NaOH / methanol / 1 h / 0 °C

4: 62 percent / aq. CF₃CO₂H / methanol / 2 h / Ambient temperature

5: 42 percent / EtSH, aq. NaOH / tetrahydrofuran / 18 h / Ambient temperature

6: 33 percent / diisopropylethylamine, DMAP / dioxane / 4 h / Ambient temperature

With dmap; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; ethanethiol; In tetrahydrofuran; 1,4-dioxane; methanol; isopropyl alcohol;
DOI:10.1021/jm9708386

Reference yield:

: 1053631-97-2
Methanesulfonic acid (1S,6R)-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-6-yl ester

: 68691-66-7
(5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione

Guidance literature:: Multi-step reaction with 5 steps

1: aq. NaOH / propan-2-ol / 0.33 h / Ambient temperature

2: 67 percent / aq. NaOH / methanol / 1 h / 0 °C

3: 62 percent / aq. CF₃CO₂H / methanol / 2 h / Ambient temperature

4: 42 percent / EtSH, aq. NaOH / tetrahydrofuran / 18 h / Ambient temperature

5: 33 percent / diisopropylethylamine, DMAP / dioxane / 4 h / Ambient temperature

With dmap; sodium hydroxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; ethanethiol; In tetrahydrofuran; 1,4-dioxane; methanol; isopropyl alcohol;
DOI:10.1021/jm9708386