Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

Base Information

Chemical Name:Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester
CAS No.:304665-06-3
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

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Chemical Property of Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

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Technology Process of Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

There total 12 articles about Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester 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: 94.0%

: 304665-05-2
Allyl-((2S,3R)-6-hydroxy-2-vinyl-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

: 304665-06-3
Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol;
DOI:10.1021/ol006384f

Reference yield:

: 221015-46-9
(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

: 304665-06-3
Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / NaBH₄; CeCl₃ / methanol / 0 °C

2: H₂ / PtO₂

3: Et₃N

4: NaN₃ / dimethylformamide / Heating

5: LiAlH₄ / tetrahydrofuran

6: K₂CO₃

7: 90 percent / NaH / dimethylformamide

8: TBAF / tetrahydrofuran

9: Et₃N

10: LiI / tetrahydrofuran

11: Zn; AcOH / ethanol

12: 94 percent / NaBH₄ / ethanol

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; 1: Reduction / 2: Catalytic hydrogenation / 3: Substitution / 4: Substitution / 5: Reduction / 6: Substitution / 7: Substitution / 8: desilylation / 9: Substitution / 10: Substitution / 11: Reduction / 12: Reduction;
DOI:10.1021/ol006384f

Reference yield:

: 221015-49-2
(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-ol

: 304665-06-3
Allyl-[(1R,2S)-2-hydroxy-1-(3-hydroxy-propyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: H₂ / PtO₂

2: Et₃N

3: NaN₃ / dimethylformamide / Heating

4: LiAlH₄ / tetrahydrofuran

5: K₂CO₃

6: 90 percent / NaH / dimethylformamide

7: TBAF / tetrahydrofuran

8: Et₃N

9: LiI / tetrahydrofuran

10: Zn; AcOH / ethanol

11: 94 percent / NaBH₄ / ethanol

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Reduction / 5: Substitution / 6: Substitution / 7: desilylation / 8: Substitution / 9: Substitution / 10: Reduction / 11: Reduction;
DOI:10.1021/ol006384f