Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester
• CAS No.: 302906-16-7
• Molecular Formula: C₂₃H₃₁NO₅S₂
• Molecular Weight: 465.635

Synonyms:Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

Chemical Property of Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

There total 11 articles about Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester 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: 92.0%

carbon disulfide (75-15-0,12122-00-8) + ((3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester (302906-15-6) + methyl iodide (74-88-4) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (302906-16-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -30 ℃;

DOI:10.1021/ol006377r

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (302906-16-7)

Guidance literature:

Multi-step reaction with 10 steps

1: NaIO₄ / methanol; H₂O

2: Mo(CO)6 / acetonitrile; H₂O

3: 49 percent / lipase AK (pseudomonas fluorescens, Amano) / CH₂Cl₂ / 48 h / 20 °C

4: 98 percent / K₂CO₃ / methanol

5: 91 percent / imidazole / dimethylformamide

6: OsO₄; NMO / tetrahydrofuran; H₂O

7: PPTS / dimethylformamide

8: NaI; NaH / tetrahydrofuran

9: TBAF / tetrahydrofuran

10: 92 percent / NaH / tetrahydrofuran / -30 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; hexacarbonyl molybdenum; lipase AK (pseudomonas fluorescens, Amano); tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Ring cleavage / 3: Acetylation / 4: Substitution / 5: silylation / 6: hydroxylation / 7: Cyclization / 8: Substitution / 9: desilylation / 10: Addition;

DOI:10.1021/ol006377r

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (302906-16-7)

Guidance literature:

Multi-step reaction with 10 steps

1: NaIO₄ / methanol; H₂O

2: Mo(CO)6 / acetonitrile; H₂O

3: 49 percent / lipase AK (pseudomonas fluorescens, Amano) / CH₂Cl₂ / 48 h / 20 °C

4: 98 percent / K₂CO₃ / methanol

5: 91 percent / imidazole / dimethylformamide

6: OsO₄; NMO / tetrahydrofuran; H₂O

7: PPTS / dimethylformamide

8: NaI; NaH / tetrahydrofuran

9: TBAF / tetrahydrofuran

10: 92 percent / NaH / tetrahydrofuran / -30 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; hexacarbonyl molybdenum; lipase AK (pseudomonas fluorescens, Amano); tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Ring cleavage / 3: Acetylation / 4: Substitution / 5: silylation / 6: hydroxylation / 7: Cyclization / 8: Substitution / 9: desilylation / 10: Addition;

DOI:10.1021/ol006377r

upstream raw materials:

carbon disulfide

((3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester

methyl iodide

Benzyl N-hydroxycarbamate

Downstream raw materials:

(3aS,3bR,6S,6aS,7aR)-6-Isopropenyl-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

(2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

1-(benzyloxycarbonyl)kainic acid dimethyl ester

(2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

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