(+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate

Base Information

• Chemical Name: (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate
• CAS No.: 126559-79-3
• Molecular Formula: C₃₁H₄₈O₃SSeSi₂
• Molecular Weight: 635.917
• Mol file: 126559-79-3.mol

Synonyms:

Chemical Property of (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate

There total 8 articles about (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate 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%

Phenylselenyl chloride (5707-04-0) + (+/-)-(E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-enoic acid (126559-78-2,129866-66-6) → (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate (126559-79-3,126559-81-7)

Guidance literature:

With triethylammonium salt; tributylphosphine; In dichloromethane; Ambient temperature;

DOI:10.1039/c39890001366

Reference yield:

(+/-)-ethyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)-hept-6-enoate (126559-76-0,126559-77-1) → (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate (126559-79-3,126559-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / KOH / methanol; H₂O

2: 73 percent / triethylammonium salt, tributylphosphine / CH₂Cl₂ / Ambient temperature

With potassium hydroxide; triethylammonium salt; tributylphosphine; In methanol; dichloromethane; water;

DOI:10.1039/c39890001366

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (+/-)-Se-phenyl (E)-3,5-anti-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-eneselenoate (126559-79-3,126559-81-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tetramethylammonium triacetoxyborohyride; 2.) imidazole / 1.) acetic acid, acetonitrile, -30 deg C; 2.) DMF

2: 86 percent / KOH / methanol; H₂O

3: 73 percent / triethylammonium salt, tributylphosphine / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; potassium hydroxide; triethylammonium salt; tributylphosphine; tetramethylammonium triacetoxyborohydride; In methanol; dichloromethane; water;

DOI:10.1039/c39890001366

upstream raw materials:

Phenylselenyl chloride

(+/-)-(E)-3,5-syn-bis(t-butyldimethylsiloxy)-7-(phenylthio)hept-6-enoic acid

(+/-)-ethyl (E)-3,5-syn-bis(t-butyldimethylsiloxy)-7-(phenylthio)-hept-6-enoate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(+/-)-trans-3,5-bis(t-butyldimethylsiloxy)-2-methylenecyclohexanone

(2RS,3SR,5SR)-3,5-bis(t-butyldimethylsiloxy)-2-(phenylthiomethyl)cyclohexanone

(2RS,3RS,5RS)-3,5-bis(t-butyldimethylsiloxy)-2-(phenylthiomethyl)cyclohexanone

(2S,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-phenylsulfanylmethyl-cyclohexanone