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

Base Information

Chemical Name:[(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane
CAS No.:452084-58-1
Molecular Formula:C₂₇H₄₁N₃O₄Si
Molecular Weight:499.726
Hs Code.:

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

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Chemical Property of [(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane

There total 11 articles about [(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane 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: 75.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 452084-63-8
(2S,3R)-1-Azido-3-benzyloxy-6-(4-methoxy-benzyloxy)-hexan-2-ol

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

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/S0040-4039(02)00681-0

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; dmap; sodium azide; dimethylsulfide borane complex; TEA; dihydrogen peroxide; sodium hydride; potassium carbonate; ammonium chloride; trifluoroacetic acid; 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

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

Guidance literature:: Multi-step reaction with 4 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

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