(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

Base Information

Chemical Name:(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol
CAS No.:452084-67-2
Molecular Formula:C₁₉H₃₃N₃O₃Si
Molecular Weight:379.575
Hs Code.:

Synonyms:(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

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Chemical Property of (4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

Chemical Property:

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Technology Process of (4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

There total 12 articles about (4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-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: 95.0%

: 452084-58-1
[(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane

: 452084-67-2
(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃;
DOI:10.1016/S0040-4039(02)00681-0

Reference yield:

: 100-39-0
benzyl bromide

: 452084-67-2
(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / NaH / tetrahydrofuran / 20 °C

2: 79 percent / BH₃-DMS; H₂O₂ / tetrahydrofuran / 0 °C

3: 89 percent / NaH / tetrahydrofuran / 20 °C

4: 93 percent / TFA / tetrahydrofuran; H₂O / 20 °C

5: TEA / CH₂Cl₂ / 0 - 20 °C

6: K₂CO₃ / methanol / 20 °C

7: 97 percent / NaN₃; NH₄Cl / dimethylformamide / 100 °C

8: 75 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

9: 95 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

With 1H-imidazole; dmap; sodium azide; dimethylsulfide borane complex; TEA; dihydrogen peroxide; sodium hydride; potassium carbonate; ammonium chloride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00681-0

Reference yield:

: 154476-70-7
6-(4-methoxybenzyloxy)hex-1-en-3-ol

: 452084-67-2
(4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 40 percent / tert-butyl-hydroperoxide; TTIP; (-)-DIPT / CH₂Cl₂ / -20 °C

2: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 20 °C

3: 97 percent / NaN₃; NH₄Cl / dimethylformamide / 100 °C

4: 75 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

5: 95 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; D-(-)-diisopropyl tartrate; ammonium chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(02)00681-0