(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

Base Information

Chemical Name:(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene
CAS No.:292074-23-8
Molecular Formula:C₂₈H₃₇N₃O₆
Molecular Weight:511.618
Hs Code.:

Synonyms:(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

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Chemical Property of (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

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Technology Process of (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

There total 10 articles about (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 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:

: 69-65-8
mannitol

: 292074-23-8
(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78 percent / ZnCl₂ / 24 h / 20 °C

2.1: NaH / various solvent(s); tetrahydrofuran / 2 h / 0 °C

2.2: 84 percent / tetrabutylammonium iodide / various solvent(s); tetrahydrofuran / 6 h / 20 °C

3.1: 38 percent / acetic acid; water / 3.5 h / 20 °C

4.1: 79 percent / NaIO₄ / H₂O; diethyl ether / 2.5 h / 20 °C

5.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C

5.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

6.1: 94 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -20 °C

7.1: 93 percent / pyridine / tetrahydrofuran / 2.5 h / 20 °C

8.1: 95 percent / aq. HCl / tetrahydrofuran / 5 h / 40 °C

9.1: 89 percent / K₂CO₃ / methanol / 2 h / 0 °C

10.1: 47 percent / NaN₃; NH₄Cl / 15-crown-5 / dimethylformamide / 10 h / 55 °C

11.1: 83 percent / ethyldiisopropylamine / 6.5 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; sodium azide; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; 15-crown-5; In tetrahydrofuran; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Metallation / 5.2: Horner-Wadsworth-Emmons reaction / 6.1: Reduction / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Ring cleavage / 11.1: Substitution;
DOI:10.1021/ol0060432

Reference yield:

: 106929-09-3
(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal

: 292074-23-8
(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C

1.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

2.1: 94 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -20 °C

3.1: 93 percent / pyridine / tetrahydrofuran / 2.5 h / 20 °C

4.1: 95 percent / aq. HCl / tetrahydrofuran / 5 h / 40 °C

5.1: 89 percent / K₂CO₃ / methanol / 2 h / 0 °C

6.1: 47 percent / NaN₃; NH₄Cl / 15-crown-5 / dimethylformamide / 10 h / 55 °C

7.1: 83 percent / ethyldiisopropylamine / 6.5 h / 20 °C

With pyridine; hydrogenchloride; sodium azide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; N-ethyl-N,N-diisopropylamine; 15-crown-5; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Horner-Wadsworth-Emmons reaction / 2.1: Reduction / 3.1: Acylation / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Ring cleavage / 7.1: Substitution;
DOI:10.1021/ol0060432

Reference yield:

: 121964-05-4
3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol

: 292074-23-8
(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / NaIO₄ / H₂O; diethyl ether / 2.5 h / 20 °C

2.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C

2.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

3.1: 94 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -20 °C

4.1: 93 percent / pyridine / tetrahydrofuran / 2.5 h / 20 °C

5.1: 95 percent / aq. HCl / tetrahydrofuran / 5 h / 40 °C

6.1: 89 percent / K₂CO₃ / methanol / 2 h / 0 °C

7.1: 47 percent / NaN₃; NH₄Cl / 15-crown-5 / dimethylformamide / 10 h / 55 °C

8.1: 83 percent / ethyldiisopropylamine / 6.5 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; sodium azide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; N-ethyl-N,N-diisopropylamine; 15-crown-5; In tetrahydrofuran; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Metallation / 2.2: Horner-Wadsworth-Emmons reaction / 3.1: Reduction / 4.1: Acylation / 5.1: Hydrolysis / 6.1: Cyclization / 7.1: Ring cleavage / 8.1: Substitution;
DOI:10.1021/ol0060432