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

Base Information

Chemical Name:(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole
CAS No.:872221-76-6
Molecular Formula:C₃₁H₄₁NO₇SSi
Molecular Weight:599.821
Hs Code.:

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

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

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

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

There total 11 articles about (3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole 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: 89.0%

: 872221-75-5
(3aS,4S,5R,6R,7R,7aS)-4-hydroxy-2,2-dimethyl-7-(4-methylphenylsulfonamido)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

: 18162-48-6
tert-butyldimethylsilyl chloride

: 872221-76-6
(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1021/ol052372o DOI:10.1139/V06-078

Reference yield:

: 160309-18-2
(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

: 872221-76-6
(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

Guidance literature:: Multi-step reaction with 6 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

4.1: dimethylformamide / 2 h / 70 °C

4.2: 33 percent / H₂SO₄ / tetrahydrofuran; H₂O / 1.5 h

5.1: 84 percent / tetrabutylammonium triphenyldifluorosilicate / acetonitrile / 4 h / 20 °C

6.1: 89 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; n-butyllithium; sulfuryl dichloride; 4-methylmorpholine N-oxide; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1139/V06-078

Reference yield:

: 872221-71-1
(3aS,4R,5R,6S,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-4-(4-methylphenylsulfonamido)-5-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

: 872221-76-6
(3aS,4S,5R,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4-(tert-butyldimethylsilyloxy)-5-phenylcarbonyloxy-6-(1-ethynyl)perhydro-1,3-benzodioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / triethylamine; SO₂Cl₂ / CH₂Cl₂ / 0 - 20 °C

2.1: dimethylformamide / 2 h / 70 °C

2.2: 33 percent / H₂SO₄ / tetrahydrofuran; H₂O / 1.5 h

3.1: 84 percent / tetrabutylammonium triphenyldifluorosilicate / acetonitrile / 4 h / 20 °C

4.1: 89 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; sulfuryl dichloride; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1139/V06-078