N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

Base Information

Chemical Name:N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide
CAS No.:211691-25-7
Molecular Formula:C₂₈H₄₁NO₆
Molecular Weight:487.637
Hs Code.:

Synonyms:N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

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Chemical Property of N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

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Technology Process of N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

There total 10 articles about N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide 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: 93.0%

: 211691-24-6
(2E,1'S,6R,3aS,6aR)-6-[10',10'-ethylenedioxy-1'-(4''-methoxybenzyloxy)hexadec-2'-en-1'-yl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

: 211691-25-7
N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; Ambient temperature;
DOI:10.1021/ja981141s

Reference yield:

: 211691-22-4
(1'S,6R,3aS,6aR)-6-[2'-hydroxy-1'-(4''-methoxybenzyloxy)ethyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

: 211691-25-7
N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

Guidance literature:: Multi-step reaction with 4 steps

1: NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 0 °C

2: CrCl₂ / tetrahydrofuran / 0 °C

3: 94 percent / (dppf)PdCl₂, Ph₃As, Cs₂CO₃ / dimethylformamide; tetrahydrofuran; H₂O / Ambient temperature

4: 93 percent / aq. CAN / acetonitrile / Ambient temperature

With chromium dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium cerium(IV) nitrate; triphenyl-arsane; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja981141s

Reference yield:

: (R)-(4-Methoxy-benzyloxy)-((3aS,6S,6aR)-3a-methyl-4-oxo-2-phenyl-3a,4,6,6a-tetrahydro-furo[3,4-d]oxazol-6-yl)-acetaldehyde

: 211691-25-7
N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

Guidance literature:: Multi-step reaction with 3 steps

1: CrCl₂ / tetrahydrofuran / 0 °C

2: 94 percent / (dppf)PdCl₂, Ph₃As, Cs₂CO₃ / dimethylformamide; tetrahydrofuran; H₂O / Ambient temperature

3: 93 percent / aq. CAN / acetonitrile / Ambient temperature

With chromium dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium cerium(IV) nitrate; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja981141s