(1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide

Base Information

• Chemical Name: (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide
• CAS No.: 155234-15-4
• Molecular Formula: C₂₄H₂₉NO₂S
• Molecular Weight: 395.566
• Mol file: 155234-15-4.mol

Synonyms:

Chemical Property of (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide

There total 10 articles about (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide 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:

(1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol (132609-85-9) → (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide (155234-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / p-toluenesulfonic acid monohydrate / benzene / 1 h / Ambient temperature

2: 92 percent / diphenylsilane, bis(butyltin)oxide, azobis(isobutyronitrile) / toluene / 3 h / 110 °C

3: N-chlorosuccinimide, NH₃ / tetrahydrofuran / 0.5 h / -33 °C

4: CH₂Cl₂; tetrahydrofuran / 28 h / Ambient temperature

5: 85percent m-chloroperoxybenzoic acid / tetrahydrofuran / 0.17 h / -78 °C

With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile); diphenylsilane; ammonia; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/jo00083a037

Reference yield:

(1R,2S,3R,4S)-3-Aminosulfanyl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (155234-10-9) → (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide (155234-15-4)

Guidance literature:

Multi-step reaction with 9 steps

1: CH₂Cl₂; tetrahydrofuran / 28 h / Ambient temperature

2: 75 percent / tetrahydrofuran / 0.5 h

3: 99 percent / 6 N aq. HCl / tetrahydrofuran / 3 h

4: LAH / tetrahydrofuran

5: 98 percent / p-toluenesulfonic acid monohydrate / benzene / 1 h / Ambient temperature

6: 92 percent / diphenylsilane, bis(butyltin)oxide, azobis(isobutyronitrile) / toluene / 3 h / 110 °C

7: N-chlorosuccinimide, NH₃ / tetrahydrofuran / 0.5 h / -33 °C

8: CH₂Cl₂; tetrahydrofuran / 28 h / Ambient temperature

9: 85percent m-chloroperoxybenzoic acid / tetrahydrofuran / 0.17 h / -78 °C

With hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); diphenylsilane; ammonia; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1021/jo00083a037

Reference yield:

(1R,2S,3R)-3-Mercapto-2-(benzyloxy)-1,7,7-trimethylbicyclo<2.2.1>heptane (155234-07-4) → (1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]heptane-2-sulfinic acid 1-phenyl-meth-(E)-ylideneamide (155234-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N-chlorosuccinimide, NH₃ / tetrahydrofuran / 0.5 h / -33 °C

2: CH₂Cl₂; tetrahydrofuran / 28 h / Ambient temperature

3: 85percent m-chloroperoxybenzoic acid / tetrahydrofuran / 0.17 h / -78 °C

With N-chloro-succinimide; ammonia; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00083a037

upstream raw materials:

(1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol

(1R,2S,3R,4S)-3-Aminosulfanyl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol

(1R,2S,3R)-3-Mercapto-2-(benzyloxy)-1,7,7-trimethylbicyclo<2.2.1>heptane

C₁₇H₂₃NOS