1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

Base Information

Chemical Name:1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose
CAS No.:792949-47-4
Molecular Formula:C₂₅H₃₁NO₈
Molecular Weight:473.523
Hs Code.:

Synonyms:1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

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Chemical Property of 1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

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Technology Process of 1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

There total 4 articles about 1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose 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:

: 3152-43-0,3945-17-3,3945-18-4,86257-92-3,89921-34-6,89921-35-7,101052-70-4
3,4-di-O-acetyl-D-arabinal

: 792949-47-4
1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaOMe / methanol / 3.25 h / 0 - 20 °C

2.1: 118 g / pyridine / 96 h

3.1: 33 percent / NaN₃; Ce(NH₄)2(NO₃)6 / acetonitrile / -25 °C

4.1: 61 percent / aq. NaNO₂ / dioxane / 5 h / 80 °C

5.1: 64 percent / PPh₃ / dioxane / 8 h / 20 °C

6.1: MeMgCl / tetrahydrofuran / 0.25 h / 0 °C

6.2: 82 percent / tetrahydrofuran / 1.25 h / -78 - 0 °C

With pyridine; sodium azide; ammonium cerium(IV) nitrate; methylmagnesium chloride; sodium methylate; triphenylphosphine; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile;
DOI:10.1055/s-2004-831173

Reference yield:

: 792949-42-9
1,5-anhydro-3,4-di-O-pivaloyl-2-deoxy-D-erythro-pent-1-enitol

: 792949-47-4
1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 33 percent / NaN₃; Ce(NH₄)2(NO₃)6 / acetonitrile / -25 °C

2.1: 61 percent / aq. NaNO₂ / dioxane / 5 h / 80 °C

3.1: 64 percent / PPh₃ / dioxane / 8 h / 20 °C

4.1: MeMgCl / tetrahydrofuran / 0.25 h / 0 °C

4.2: 82 percent / tetrahydrofuran / 1.25 h / -78 - 0 °C

With sodium azide; ammonium cerium(IV) nitrate; methylmagnesium chloride; triphenylphosphine; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; acetonitrile;
DOI:10.1055/s-2004-831173

Reference yield:

: 792949-43-0
2-azido-2-deoxy-3,4-di-O-pivaloyl-D-arabinopyranosyl nitrate

: 792949-47-4
1,2-dideoxy-1,2-[(E)-N-(3-phenyl-2-propenoyl)epoxycarbonylimino]-3,4-di-O-pivaloyl-β-D-arabinopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 61 percent / aq. NaNO₂ / dioxane / 5 h / 80 °C

2.1: 64 percent / PPh₃ / dioxane / 8 h / 20 °C

3.1: MeMgCl / tetrahydrofuran / 0.25 h / 0 °C

3.2: 82 percent / tetrahydrofuran / 1.25 h / -78 - 0 °C

With methylmagnesium chloride; triphenylphosphine; sodium nitrite; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1055/s-2004-831173