6H-1,3-Oxazin-6-one, tetrahydro-3-[(4-methylphenyl)sulfonyl]-4-[(phenylmethoxy)methyl]-, (4S)-

Base Information

• Chemical Name: 6H-1,3-Oxazin-6-one, tetrahydro-3-[(4-methylphenyl)sulfonyl]-4-[(phenylmethoxy)methyl]-, (4S)-
• CAS No.: 905859-22-5
• Molecular Formula: C₁₉H₂₁NO₅S
• Molecular Weight: 375.445
• Mol file: 905859-22-5.mol

Synonyms:

Chemical Property of 6H-1,3-Oxazin-6-one, tetrahydro-3-[(4-methylphenyl)sulfonyl]-4-[(phenylmethoxy)methyl]-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6H-1,3-Oxazin-6-one, tetrahydro-3-[(4-methylphenyl)sulfonyl]-4-[(phenylmethoxy)methyl]-, (4S)-

There total 1 articles about 6H-1,3-Oxazin-6-one, tetrahydro-3-[(4-methylphenyl)sulfonyl]-4-[(phenylmethoxy)methyl]-, (4S)- 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:

(2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)pyrrolidin-4-one (905859-13-4) → 4-benzyloxymethyl-3-(toluene-4-sulfonyl)-[1,3]oxazinan-6-one (905859-22-5)

Guidance literature:

With sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.3987/COM-06-10874

Reference yield:

4-benzyloxymethyl-3-(toluene-4-sulfonyl)-[1,3]oxazinan-6-one (905859-22-5) → (2S)-N-(1-benzyloxymethyl-3-hydroxypropyl)-4-methylbenzenesulfonamide (115344-32-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.3987/COM-06-10874

Reference yield:

4-benzyloxymethyl-3-(toluene-4-sulfonyl)-[1,3]oxazinan-6-one (905859-22-5) → [1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol (919116-91-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 270 mg / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

2: 95 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: 92 percent / NaH / dimethylformamide / 3 h / 20 °C

4: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5: 87 percent / pyridinium chlorochromate; Celite / CH₂Cl₂ / 20 h / 20 °C

6: 80 percent / n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C

7: 88 percent / Grubbs' 2nd generation catalyst / CH₂Cl₂ / 2 h / Heating

8: 87 percent / boron tribromide / CH₂Cl₂ / 3 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; Celite; tetrabutyl ammonium fluoride; boron tribromide; sodium hydride; pyridinium chlorochromate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 6: Wittig olefination;

DOI:10.3987/COM-06-10874

upstream raw materials:

(2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)pyrrolidin-4-one

Downstream raw materials:

(2S)-N-(1-benzyloxymethyl-3-hydroxypropyl)-4-methylbenzenesulfonamide

N-allyl-N-(1-benzyloxymethyl-3-oxopropyl)-4-methylbenzenesulfonamide

(2S)-N-allyl-N-[1-benzyloxymethyl-3-(t-butyldimethylsilanyloxy)propyl]-4-methylbenzenesulfonamide

[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol