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

Base Information

Chemical Name:(3R)-3-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]-3-(benzyloxy)propanal
CAS No.:1447810-32-3
Molecular Formula:C₁₇H₂₁N₃O₅
Molecular Weight:347.371
Hs Code.:

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

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

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

There total 3 articles about (3R)-3-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]-3-(benzyloxy)propanal 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%

: 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

Reference yield:

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

: 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:: Multi-step reaction with 3 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

3.1: ozone / dichloromethane / -78 °C

3.2: 24 h / 25 °C / Inert atmosphere

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

Reference yield:

: 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

: 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:: Multi-step reaction with 2 steps

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

1.2: 4 h / 0 - 25 °C

2.1: ozone / dichloromethane / -78 °C

2.2: 24 h / 25 °C / Inert atmosphere

With sodium hydride; ozone; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1021/jo400448p