(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

Base Information

Chemical Name:(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol
CAS No.:913355-82-5
Molecular Formula:C₂₅H₃₆ClNO₆
Molecular Weight:482.017
Hs Code.:

Synonyms:(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

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Chemical Property of (4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

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Technology Process of (4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

There total 8 articles about (4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol 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:

: 913355-81-4
(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-triethylsilanyloxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-6-(tert-butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

: 913355-82-5
(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

Guidance literature:: With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200601655

Reference yield:

: (S)-2-Methyl-4-triisopropylsilanyloxy-butyraldehyde oxime

: 913355-82-5
(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tert-BuOCl / CH₂Cl₂ / -78 °C

1.2: EtMgBr / CH₂Cl₂; propan-2-ol

2.1: tetra-n-butylammonium fluoride / tetrahydrofuran

3.1: 83 percent / iodine; imidazole; triphenylphosphine / tetrahydrofuran

4.1: 92 percent / 2,6-lutidine / tetrahydrofuran

5.1: lithium diisopropylamide / tetrahydrofuran / -78 °C

5.2: tetrahydrofuran

6.1: tris(dimethylamino)sulfonium difluorotrimethylsilicate / H₂O; dimethylformamide

With 1H-imidazole; 2,6-dimethylpyridine; tert-butylhypochlorite; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200601655

Reference yield:

: 913355-71-2
(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butan-1-ol

: 913355-82-5
(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-hydroxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-5-chloro-4-methoxy-6-vinyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / iodine; imidazole; triphenylphosphine / tetrahydrofuran

2.1: 92 percent / 2,6-lutidine / tetrahydrofuran

3.1: lithium diisopropylamide / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran

4.1: tris(dimethylamino)sulfonium difluorotrimethylsilicate / H₂O; dimethylformamide

With 1H-imidazole; 2,6-dimethylpyridine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200601655