(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

Base Information

Chemical Name:(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
CAS No.:211691-24-6
Molecular Formula:C₃₈H₅₁NO₇
Molecular Weight:633.825
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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%

: 344615-56-1
2-[6-(9-Bora-bicyclo[3.3.1]non-9-yl)-hexyl]-2-hexyl-[1,3]dioxolane

: 211691-23-5
(2'E,1'S,6R,3aS,6aR)-6-[3'-iodo-1'-(4''methoxybenzyloxy)-2'-propen-1'-yl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

: 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

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/ja981141s

Reference yield:

: 211691-13-3
methyl (2S,3R,4E)-3-acetoxy-2-benzamido-2-methyl-6-(tertbutyldiphenylsilyloxy)-4-hexenoate

: 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

Guidance literature:: Multi-step reaction with 8 steps

1: aq. OsO₄; NMO / CH₂Cl₂ / 16 h / 25 °C

2: (S)-(+)-camphorsulfonic acid / CH₂Cl₂ / 24 h / 25 °C

3: 93 percent / K₂CO₃ / methanol; CH₂Cl₂ / 0.5 h / 20 °C

4: Tf₂O; pyridine; DMAP / 1,2-dichloro-ethane / 2 h / Heating

5: 99 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

6: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

7: 88.7 mg / CrCl₂ / tetrahydrofuran / 8 h / 0 - 20 °C

8: (dppf)PdCl₂; Ph₃As; aq. Cs₂CO₃ / dimethylformamide / 4 h / 25 °C

With pyridine; chromium dichloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; N-methyl-2-indolinone; trifluoromethylsulfonic anhydride; triphenyl-arsane; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 7: Takai-Utimoto olefination / 8: Suzuki coupling;
DOI:10.1021/ja0118338

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

: 211691-24-6
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 88.7 mg / CrCl₂ / tetrahydrofuran / 8 h / 0 - 20 °C

2: (dppf)PdCl₂; Ph₃As; aq. Cs₂CO₃ / dimethylformamide / 4 h / 25 °C

With chromium dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Takai-Utimoto olefination / 2: Suzuki coupling;
DOI:10.1021/ja0118338