(3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester
• CAS No.: 107961-27-3
• Molecular Formula: C₁₈H₂₀O₇S
• Molecular Weight: 380.419
• Mol file: 107961-27-3.mol

Synonyms:(3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester

Chemical Property of (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester

There total 4 articles about (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid 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: 69.0%

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-26-2) → (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ4-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester (107961-27-3)

Guidance literature:

rhodium(II) acetate; In dichloromethane; for 2h; Heating;

DOI:10.1021/ja00244a024

Reference yield:

β-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-37-5) → (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ4-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester (107961-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 30.4 percent / tri-n-butylphosphine / CH₂Cl₂ / 3 h / Ambient temperature

2: 85 percent / Et₃N, p-toluenesulfonyl azide / acetonitrile / 4 h / Ambient temperature

3: 69 percent / rhodium acetate / CH₂Cl₂ / 2 h / Heating

With 4-toluenesulfonyl azide; tributylphosphine; triethylamine; rhodium(II) acetate; In dichloromethane; acetonitrile;

DOI:10.1021/ja00244a024

Reference yield:

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-25-1) → (3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ4-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester (107961-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N, p-toluenesulfonyl azide / acetonitrile / 4 h / Ambient temperature

2: 69 percent / rhodium acetate / CH₂Cl₂ / 2 h / Heating

With 4-toluenesulfonyl azide; triethylamine; rhodium(II) acetate; In dichloromethane; acetonitrile;

DOI:10.1021/ja00244a024

upstream raw materials:

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

β-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

diphenyldisulfane

Downstream raw materials:

[(3aS,5aR,8aR,8bS)-7,7-Dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-(2Z)-ylidene]-phenylsulfanyl-acetic acid methyl ester

[(3aS,5aR,8aR,8bS)-7,7-Dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-(2E)-ylidene]-phenylsulfanyl-acetic acid methyl ester