(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

Base Information

Chemical Name:(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol
CAS No.:287205-38-3
Molecular Formula:C₂₉H₃₅N₃O₃Si
Molecular Weight:501.701
Hs Code.:

Synonyms:(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

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Chemical Property of (2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

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Technology Process of (2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

There total 6 articles about (2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol 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: 86.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 287205-37-2
(2S,3S)-3-azido-3-[1-(benzyloxy)cyclopropyl]-1,2-propanediol

: 287205-38-3
(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(00)00369-0

Reference yield:

: 100-39-0
benzyl bromide

: 287205-38-3
(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / NaH; n-Bu₄NI; imidazole / tetrahydrofuran / 18 h / 50 °C

2: 57 percent / aq. TFA / dioxane / 48 h / 20 °C

3: 86 percent / DMAP; imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Etherification / 2: Hydrolysis / 3: Condensation;
DOI:10.1016/S0040-4020(00)00369-0

Reference yield:

: 287205-32-7
(S)-4-cyclopropylidene-2,2-dimethyl-1,3-dioxolane

: 287205-38-3
(2S,3S)-1-azido-1-[1-(benzyloxy)cyclopropyl]-3-{[tert-butyl(diphenyl)silyl]oxy}-2-propanol

Guidance literature:: Multi-step reaction with 5 steps

1: 49 percent / m-CPBA / CH₂Cl₂ / 0 - 20 °C

2: 74 percent / NaN₃; H₂O; NH₄Cl / methanol / 12 h / 80 °C

3: 50 percent / NaH; n-Bu₄NI; imidazole / tetrahydrofuran / 18 h / 50 °C

4: 57 percent / aq. TFA / dioxane / 48 h / 20 °C

5: 86 percent / DMAP; imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; dmap; sodium azide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1: Epoxidation / 2: Ring cleavage / 3: Etherification / 4: Hydrolysis / 5: Condensation;
DOI:10.1016/S0040-4020(00)00369-0