(3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole

Base Information

• Chemical Name: (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole
• CAS No.: 212645-37-9
• Molecular Formula: C₂₉H₃₁NO₄S
• Molecular Weight: 489.635

Synonyms:(3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole

Chemical Property of (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole

There total 15 articles about (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole 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:

5-(2,2-dibromovinyl)-1,3-benzodioxol (92449-54-2) → (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole (212645-37-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) BuLi / 1.) THF, -78 deg C, 1 h; r.t., 1.5 h, 2.) THF, -78 deg C, 0.5 h; r.t., 0.5 h

2: 1.) Bu₃SnH, 2.) BuLi / 1.) Pd(PPh₃)4 / 1.) C₆H₆, r.t., 14 h, 2.) THF, -78 deg C, 0.5 h

3: 1.) tert-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 45 min

4: 100 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) r.t., 14 h

5: 92 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 2.) -25 deg C, 24 h

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

7: 1.) molecular sieves 4 Angstroem, 2.) BuLi / 1.) Et₂O, r.t., 16 h, 2.) THF, -78 deg C, 2 h

With n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; ethanethiol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8

Reference yield:

diphenyldisulfane (882-33-7) → (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole (212645-37-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) BuLi / 1.) THF, -78 deg C, 1 h; r.t., 1.5 h, 2.) THF, -78 deg C, 0.5 h; r.t., 0.5 h

2: 1.) Bu₃SnH, 2.) BuLi / 1.) Pd(PPh₃)4 / 1.) C₆H₆, r.t., 14 h, 2.) THF, -78 deg C, 0.5 h

3: 1.) tert-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 45 min

4: 100 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) r.t., 14 h

5: 92 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 2.) -25 deg C, 24 h

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

7: 1.) molecular sieves 4 Angstroem, 2.) BuLi / 1.) Et₂O, r.t., 16 h, 2.) THF, -78 deg C, 2 h

With n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; ethanethiol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8

Reference yield:

5-Phenylsulfanylethynyl-benzo[1,3]dioxole (212645-16-4) → (3S,3aS,5S,6S,7aR)-3-Benzo[1,3]dioxol-5-yl-6-benzyloxy-5-methoxy-3a-phenylsulfanyl-octahydro-indole (212645-37-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Bu₃SnH, 2.) BuLi / 1.) Pd(PPh₃)4 / 1.) C₆H₆, r.t., 14 h, 2.) THF, -78 deg C, 0.5 h

2: 1.) tert-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 45 min

3: 100 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) r.t., 14 h

4: 92 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 2.) -25 deg C, 24 h

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 2.) CH₂Cl₂

6: 1.) molecular sieves 4 Angstroem, 2.) BuLi / 1.) Et₂O, r.t., 16 h, 2.) THF, -78 deg C, 2 h

With n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; ethanethiol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8

upstream raw materials:

5-(2,2-dibromovinyl)-1,3-benzodioxol

(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

diphenyldisulfane

methyl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Downstream raw materials:

C₂₃H₂₅NO₄S

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