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

Base Information

Chemical Name:(3aS,4S,5S,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4,5-di(phenylcarbonyloxy)-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole
CAS No.:872221-78-8
Molecular Formula:C₃₅H₃₉NO₈SSi
Molecular Weight:661.848
Hs Code.:

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

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

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

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

There total 9 articles about (3aS,4S,5S,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4,5-di(phenylcarbonyloxy)-6-(2-trimethylsilyl-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: 80.0%

: 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

: 98-88-4
benzoyl chloride

: 872221-78-8
(3aS,4S,5S,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4,5-di(phenylcarbonyloxy)-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

Guidance literature:: With pyridine; at 0 - 20 ℃;
DOI:10.1021/ol052372o

Reference yield:

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

: 872221-78-8
(3aS,4S,5S,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4,5-di(phenylcarbonyloxy)-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

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: 80 percent / pyridine / 1.5 h / 20 °C

With pyridine; osmium(VIII) oxide; n-butyllithium; 4-methylmorpholine N-oxide; In dichloromethane; toluene;
DOI:10.1139/V06-078

Reference yield:

: 872221-70-0
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

: 872221-78-8
(3aS,4S,5S,6R,7R,7aS)-2,2-dimethyl-7-(4-methylphenylsulfonamido)-4,5-di(phenylcarbonyloxy)-6-(2-trimethylsilyl-1-ethynyl)perhydro-1,3-benzodioxole

Guidance literature:: Multi-step reaction with 2 steps

1: 46 percent / N-methylmorpholine-N-oxide; OsO₄ / CH₂Cl₂ / 3 h / 20 °C

2: 80 percent / pyridine / 1.5 h / 20 °C

With pyridine; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane;
DOI:10.1139/V06-078