(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

Base Information

Chemical Name:(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
CAS No.:211691-22-4
Molecular Formula:C₂₂H₂₃NO₆
Molecular Weight:397.428
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 99.0%

: 211691-21-3
(1'S, 6R,3aS,6aR)-6-[2'-tert-butyldiphenylsilyloxy-1'-(4''-methoxybenzyloxy)ethyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; 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

: 211691-22-4
(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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; potassium carbonate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja0118338

Reference yield:

: 211691-15-5
(1'S,3S,4S,5R)-3-methyl-3-benzamido-4-acetoxy-5-(2'-tert-butyldiphenylsilyloxy-1'-hydroxyethyl)oxolan-2-one

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

2: 93 percent / K₂CO₃ / methanol; CH₂Cl₂ / 0.5 h / 20 °C

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

4: 99 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With pyridine; dmap; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; potassium carbonate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja0118338