acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester

Base Information

• Chemical Name: acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester
• CAS No.: 350032-51-8
• Molecular Formula: C₂₉H₃₅F₃N₂O₉S
• Molecular Weight: 644.666

Synonyms:acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester

Chemical Property of acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester

There total 7 articles about acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl 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: 73.0%

acetic acid 7-bromo-5S-[[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester (350032-49-4) → acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester (350032-51-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran;

Reference yield:

(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (163082-04-0) → acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester (350032-51-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NH₃; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 50 °C

1.2: 94 percent / dioxane / 3 h / 60 - 70 °C

2.1: 93 percent / pyridine / DMAP / CH₂Cl₂ / 5 h / 20 °C

3.1: 98 percent / pyridine / DMAP / CH₂Cl₂ / 3 h / Heating

4.1: 73 percent / Bu₃SnH / AIBN / tetrahydrofuran / 2 h / Heating

With pyridine; ammonia; tri-n-butyl-tin hydride; ytterbium(III) triflate; dmap; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0205378

Reference yield:

acetic acid 7-bromo-5S-[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-ylamino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester (350032-67-6) → acetic acid 5S-[[2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4-yl ester (350032-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine / DMAP / CH₂Cl₂ / 3 h / Heating

2: 73 percent / Bu₃SnH / AIBN / tetrahydrofuran / 2 h / Heating

With pyridine; tri-n-butyl-tin hydride; dmap; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0205378

upstream raw materials:

acetic acid 7-bromo-5S-[[7-bromo-2,2-dimethyl-4S-(toluene-4-sulfonylamino)-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-5S-yl]-(2,2,2-trifluoro-acetyl)-amino]-2,2-dimethyl-3Ra,4S,5S,7a-tetrahydro-benzo[1S,3R]dioxol-4S-yl ester

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

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

Downstream raw materials:

acetic acid 2,2,7-trimethyl-5-[[2,2,7,7-tetramethyl-5S-(toluene-4-sulfonylamino)-hexahydro-benzo[1,2-d;3,4-d']bis[1S,3R]dioxol-4S-yl]-(2,2,2-trifluoro-acetyl)-amino]-hexahydro-benzo[1,2-d;3,4-d']bis[1S,3R]dioxol-4S-yl ester

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