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

Base Information

Chemical Name:(3aS,4R,6S,7aR)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one
CAS No.:872182-75-7
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

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

There total 9 articles about (3aS,4R,6S,7aR)-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: 84.0%

: 872182-73-5
methyl 6-C-methyl-3-(3-phenyl-propylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside

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

: 872182-75-7
(3aS,4R,6S,7aR)-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

: 872182-75-7
(3aS,4R,6S,7aR)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / pyridine / 12 h / 0 - 20 °C

2: 80 percent / sodium azide / dimethylformamide / 1.5 h / 160 °C

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

4: sodium cyanoborohydride; acetic acid / methanol / 12 h

5: 80 percent / hydrogen / palladium(II) hydroxide on carbon / ethyl acetate / 14 h

6: 84 percent / triethylamine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; sodium azide; hydrogen; sodium cyanoborohydride; acetic acid; triethylamine; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 3: Staudinger reduction;
DOI:10.1139/v05-095

Reference yield:

: (2R,3S,4R,6S)-3-Benzyloxy-2-ethyl-6-methoxy-tetrahydro-pyran-4-ylamine

: 872182-75-7
(3aS,4R,6S,7aR)-4-Ethyl-6-methoxy-1-(3-phenyl-propyl)-hexahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: sodium cyanoborohydride; acetic acid / methanol / 12 h

2: 80 percent / hydrogen / palladium(II) hydroxide on carbon / ethyl acetate / 14 h

3: 84 percent / triethylamine / CH₂Cl₂ / 5 h / 20 °C

With hydrogen; sodium cyanoborohydride; acetic acid; triethylamine; palladium dihydroxide; In methanol; dichloromethane; ethyl acetate;
DOI:10.1139/v05-095