(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Base Information

Chemical Name:(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one
CAS No.:872182-97-3
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

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Chemical Property of (3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

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Technology Process of (3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

There total 13 articles about (3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one 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: 91.0%

: 872182-92-8
methyl 6-C-methyl-3-(3-phenyl-propylamino)-2,3,6-trideoxy-α-D-ribo-hexopyranoside

: 530-62-1
1,1'-carbonyldiimidazole

: 872182-97-3
(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1139/v05-095

Reference yield:

: 872182-68-8
methyl 4-O-benzyl-2,6-dideoxy-6-C-methyl-α-D-ribo-hexopyranoside

: 872182-97-3
(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

2: 93 percent / sodium methoxide; methanol / 10 h / 20 °C

3: 97 percent / pyridine / 12 h / 0 - 20 °C

4: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 10 h

5: 76 percent / sodium azide / dimethylformamide / 12 h / 125 °C

6: 94 percent / sodium hydride / dimethylformamide; toluene / 6 h / 0 - 20 °C

7: trimethylphosphine / tetrahydrofuran; toluene; H₂O / 0.75 h / Heating

8: sodium cyanoborohydride; acetic acid / methanol / 12 h / 20 °C

9: 89 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 12 h / 20 °C

10: 91 percent / triethylamine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; methanol; sodium azide; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; hydrogen; sodium methylate; sodium hydride; sodium cyanoborohydride; acetic acid; triethylamine; triphenylphosphine; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 7: Staudinger reduction;
DOI:10.1139/v05-095

Reference yield:

: 872182-82-6
methyl 4-O-benzyl-2,6-dideoxy-6-C-methyl-α-D-arabino-hexopyranoside

: 872182-97-3
(3aS,4R,6S,7aS)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / pyridine / 12 h / 0 - 20 °C

2: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 10 h

3: 76 percent / sodium azide / dimethylformamide / 12 h / 125 °C

4: 94 percent / sodium hydride / dimethylformamide; toluene / 6 h / 0 - 20 °C

5: trimethylphosphine / tetrahydrofuran; toluene; H₂O / 0.75 h / Heating

6: sodium cyanoborohydride; acetic acid / methanol / 12 h / 20 °C

7: 89 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 12 h / 20 °C

8: 91 percent / triethylamine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; sodium azide; ammonium cerium(IV) nitrate; hydrogen; sodium hydride; sodium cyanoborohydride; acetic acid; triethylamine; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Staudinger reduction;
DOI:10.1139/v05-095