(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Base Information

Chemical Name:(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
CAS No.:90661-43-1
Molecular Formula:C₁₆H₁₉N₃O₅
Molecular Weight:333.344
Hs Code.:

Synonyms:(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

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Chemical Property of (3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

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Technology Process of (3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

There total 11 articles about (3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 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: 87.0%

: (S)-2-(benzyloxy)-1-((3aR,4S,6aR)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethyl methanesulfonate

: 90661-43-1
(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 16h; Inert atmosphere;
DOI:10.1039/c4ra06884j

Reference yield: 71.0%

: Toluene-4-sulfonic acid (S)-2-benzyloxy-1-((3aR,4S,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester

: 90661-43-1
(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Guidance literature:: With lithium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 80 ℃;
DOI:10.1246/cl.1984.405

Reference yield:

: 90661-40-8
(S)-5-((S)-2'-(benzyloxy)-1-hydroxyethyl)furan-2(5H)-one

: 90661-43-1
(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: KMnO₄ / dicyclohexano-18-crown-6 / CH₂Cl₂ / -42 °C

3: p-TsOH / CH₂Cl₂ / Ambient temperature

4: 75 percent / KF / n-Bu₄N(+)*HSO₄(-) / H₂O; CH₂Cl₂

5: Et₃N / Ambient temperature

6: 71 percent / LiN₃ / hexamethylphosphoric acid triamide / 80 °C

With 2,6-dimethylpyridine; potassium fluoride; potassium permanganate; lithium azide; triethylamine; perhydrodibenzo-18-crown-6; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1246/cl.1984.405