(3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide
• CAS No.: 872221-72-2
• Molecular Formula: C₂₁H₂₉NO₈S₂Si
• Molecular Weight: 515.681

Synonyms:(3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide

Chemical Property of (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide

There total 8 articles about (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ⁶-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide 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: 82.0%

(3aS,4R,5R,6S,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-4-(4-methylphenylsulfonamido)-5-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole (872221-71-1) → (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ6-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide (872221-72-2)

Guidance literature:

With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1021/ol052372o

Reference yield:

(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (160309-18-2) → (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ6-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide (872221-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / toluene / 0.17 h / 0 °C

1.2: AlCl₃ / toluene / 18 h / 0 - 20 °C

2.1: 46 percent / N-methylmorpholine-N-oxide; OsO₄ / CH₂Cl₂ / 3 h / 20 °C

3.1: 82 percent / triethylamine; SO₂Cl₂ / CH₂Cl₂ / 0 - 20 °C

With osmium(VIII) oxide; n-butyllithium; sulfuryl dichloride; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; toluene;

DOI:10.1139/V06-078

Reference yield:

N-((1R,2R,5R,6S)-5,6-Dihydroxy-2-trimethylsilanylethynyl-cyclohex-3-enyl)-4-methyl-benzenesulfonamide → (3aS,4R,5R,5aS,8aS,8bS)-N-(7,7-dimethyl-2,2-dioxo-4-(trimethylsilanylethynyl)hexahydro-1,3,6,8-tetraoxa-2λ6-thia-as-indacen-5-yl)-4-methylbenzenesulfonamide (872221-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.14 mmol / p-toluenesulfonic acid / acetone / 0.25 h / 20 °C

2: 46 percent / N-methylmorpholine-N-oxide; OsO₄ / CH₂Cl₂ / 3 h / 20 °C

3: 82 percent / triethylamine; SO₂Cl₂ / CH₂Cl₂ / 0 - 20 °C

With osmium(VIII) oxide; sulfuryl dichloride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; acetone;

DOI:10.1139/V06-078

upstream raw materials:

(3aS,4R,5R,6S,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-4-(4-methylphenylsulfonamido)-5-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-propioloyl-4-methylbenzenesulfonamide

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

Downstream raw materials:

(3aS,4S,5R,6R,7R,7aS)-4-hydroxy-2,2-dimethyl-7-(4-methylphenylsulfonamido)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenyl(2-propynyl)sulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

(3aS,4S,5R,6R,7R,7aS)-4-hydroxy-2,2-dimethyl-7-(4-methylphenylsulfonamido)-5-phenylcarbonyloxy-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

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