3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol

Base Information

• Chemical Name: 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol
• CAS No.: 117626-59-2
• Molecular Formula: C₁₆H₂₀O₂S
• Molecular Weight: 276.4
• Mol file: 117626-59-2.mol

Synonyms:3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol

Chemical Property of 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol

There total 11 articles about 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol 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: 98.0%

2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane (117626-58-1) → 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol (117626-59-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/jo00262a024

Reference yield:

2-<2-(phenylthio)ethyl>-1,3-dioxolane (56161-48-9) → 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol (117626-59-2)

Guidance literature:

Multi-step reaction with 11 steps

1: N-chlorosuccinimide / CCl₄ / 3 h / 25 °C

2: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C

3: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

4: d-camphorsulfonic acid / methanol / 2 h / 25 °C

5: CHCl₃ / 12 h / 25 °C

6: H₂ / 5percent Pd/C / ethyl acetate / 2.5 h / 2844.3 Torr

7: 75 percent / LiAlH₄ / tetrahydrofuran / 20 h / 40 °C

8: 1.) NaH / 1.) THF

9: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2a.) -60 deg C, 5 min, 2b.) from -60 deg C to 25 deg C

10: tetrahydrofuran / 1.5 h / 25 °C

11: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 25 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; chloroform; ethyl acetate;

DOI:10.1021/jo00262a024

Reference yield:

(+/-)-2-<2-chloro-2-(phenylthio)ethyl>-1,3-dioxolane (117626-71-8) → 3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2-exo-methanol (117626-59-2)

Guidance literature:

Multi-step reaction with 10 steps

1: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C

2: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

3: d-camphorsulfonic acid / methanol / 2 h / 25 °C

4: CHCl₃ / 12 h / 25 °C

5: H₂ / 5percent Pd/C / ethyl acetate / 2.5 h / 2844.3 Torr

6: 75 percent / LiAlH₄ / tetrahydrofuran / 20 h / 40 °C

7: 1.) NaH / 1.) THF

8: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2a.) -60 deg C, 5 min, 2b.) from -60 deg C to 25 deg C

9: tetrahydrofuran / 1.5 h / 25 °C

10: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 25 °C

With lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; ethyl acetate;

DOI:10.1021/jo00262a024

upstream raw materials:

2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane

2-<2-(phenylthio)ethyl>-1,3-dioxolane

(+/-)-2-<2-chloro-2-(phenylthio)ethyl>-1,3-dioxolane

(+/-)-(E)-4-(1,3-dioxolan-2-yl)-3-(phenylthio)-3-buten-2-ol

Downstream raw materials:

(1R,2S,3R,4R,5R)-4-Methyl-5-phenylsulfanyl-3-vinyl-7-oxa-bicyclo[2.2.1]heptane-2-carbaldehyde

2-exo,3-exo-diethenyl-4-methyl-5-(phenylthio)-7-oxabicyclo<2.2.1>heptane