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

Base Information

• Chemical Name: 2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane
• CAS No.: 117626-58-1
• Molecular Formula: C₂₂H₃₄O₂SSi
• Molecular Weight: 390.662
• Mol file: 117626-58-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane 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:

2-<2-(phenylthio)ethyl>-1,3-dioxolane (56161-48-9) → 2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane (117626-58-1)

Guidance literature:

Multi-step reaction with 10 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

With N-chloro-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; 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) → 2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane (117626-58-1)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1021/jo00262a024

Reference yield:

(+/-)-(E)-4-(1,3-dioxolan-2-yl)-3-(phenylthio)-3-buten-2-ol (117626-72-9) → 2-exo-<(tert-butyldimethylsiloxy)methyl>-3-exo-ethenyl-4-methyl-5-endo-(phenylthio)-7-oxabicyclo<2.2.1>heptane (117626-58-1)

Guidance literature:

Multi-step reaction with 7 steps

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

2: CHCl₃ / 12 h / 25 °C

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

4: 75 percent / LiAlH₄ / tetrahydrofuran / 20 h / 40 °C

5: 1.) NaH / 1.) THF

6: 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

7: tetrahydrofuran / 1.5 h / 25 °C

With lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; ethyl acetate;

DOI:10.1021/jo00262a024

upstream raw materials:

(1S,2S,3S,4S,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-6-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carbaldehyde

Methylenetriphenylphosphorane

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

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

Downstream raw materials:

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

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

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