[3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine

Base Information

• Chemical Name: [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine
• CAS No.: 305815-86-5
• Molecular Formula: C₂₀H₂₃NO₇S
• Molecular Weight: 421.471

Synonyms:[3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine

Chemical Property of [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine

Chemical Property:

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Technology Process of [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine

There total 3 articles about [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine 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: 42.0%

[3S,6R,(S)R]-N-benzyloxycarbonyl-3,6-dihydro-3-methyl-6-(p-tolylsulfinyl)-2H-1,2-oxazine → [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine (305815-86-5)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; at 20 ℃; for 48h;

DOI:10.1021/ol0063611

Reference yield:

benzyl nitrosoformat (88818-16-0) → [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine (305815-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / CH₂Cl₂ / 4 h / 0 °C

2: 42 percent / OsO₄; NMO / acetone; H₂O / 48 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; In dichloromethane; water; acetone; 1: Diels-Alder cycloaddition / 2: Oxidation;

DOI:10.1021/ol0063611

Reference yield:

(1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-1,3-pentadiene (139024-87-6) → [3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-4,5-dihydroxy-3-methyl-6-(p-tolylsulfonyl)-1,2-oxazine (305815-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / CH₂Cl₂ / 4 h / 0 °C

2: 42 percent / OsO₄; NMO / acetone; H₂O / 48 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; In dichloromethane; water; acetone; 1: Diels-Alder cycloaddition / 2: Oxidation;

DOI:10.1021/ol0063611

upstream raw materials:

benzyl nitrosoformat

(1E,3E)-(+)-(R)-1-(p-tolylsulfinyl)-1,3-pentadiene

Downstream raw materials:

(3aS,4R,7S,7aS)-2,2,7-Trimethyl-4-(toluene-4-sulfonyl)-tetrahydro-1,3,5-trioxa-6-aza-indene

[3S,4S,5S,6R]-N-benzyloxycarbonyl-3,4,5,6-tetrahydro-3-methyl-4,5-(dimethylmethylenedioxy)-6-(p-tolylsulfonyl)-1,2-oxazine

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