(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Name:(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:1447810-31-2
Molecular Formula:C₁₈H₂₃N₃O₄
Molecular Weight:345.398
Hs Code.:

Synonyms:(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 2 articles about (3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 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: 76.0%

: 1447810-30-1
(1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]but-3-en-1-ol

: 100-39-0
benzyl bromide

: 1447810-31-2
(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: (1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]but-3-en-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 0.166667h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 4h;
DOI:10.1021/jo400448p

Reference yield:

: 28072-61-9
3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose

: 1447810-31-2
(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1.1: ammonium chloride; zinc / water; tetrahydrofuran / 7 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 25 °C

2.2: 4 h / 0 - 25 °C

With sodium hydride; ammonium chloride; zinc; In tetrahydrofuran; water; mineral oil; 1.1: |Barbier Coupling Reaction;
DOI:10.1021/jo400448p

Reference yield: 87.0%

: 1447810-31-2
(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 1447810-32-3
(3R)-3-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]-3-(benzyloxy)propanal

Guidance literature:: (3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; at 25 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jo400448p