(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

Base Information

Chemical Name:(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
CAS No.:211691-23-5
Molecular Formula:C₂₃H₂₂INO₅
Molecular Weight:519.336
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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:

: 75-47-8
iodoform

: (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

: 211691-23-5
(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

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 0 ℃; Yield given;
DOI:10.1021/ja981141s

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; chromium dichloride; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium 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; 7: Takai-Utimoto olefination;
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

: 211691-23-5
(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

Guidance literature:: Multi-step reaction with 6 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

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

6: 88.7 mg / CrCl₂ / tetrahydrofuran / 8 h / 0 - 20 °C

With pyridine; chromium dichloride; dmap; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium 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; 6: Takai-Utimoto olefination;
DOI:10.1021/ja0118338