thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester

Base Information

• Chemical Name: thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester
• CAS No.: 213408-30-1
• Molecular Formula: C₂₉H₃₇NO₄S₂
• Molecular Weight: 527.749

Synonyms:thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester

Chemical Property of thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester

Chemical Property:

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Technology Process of thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester

There total 3 articles about thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethyl} ester 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: 63.0%

phenylcarbonochloridothioate (1005-56-7) + 1-[12-(Toluene-4-sulfonyl)-12-aza-bicyclo[9.2.1]tetradec-1(14)-en-2-yl]-ethanol (213408-45-8) → thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1(14)-en-2-yl]ethyl} ester (213408-30-1)

Guidance literature:

With pyridine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/ja981183g

Reference yield:

1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradeca-1(14),2-dien-2-yl]ethanone → thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1(14)-en-2-yl]ethyl} ester (213408-30-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / Pd(PPh₃)4, glacial HOAc, n-Bu₃SnH / benzene / 3 h / Ambient temperature

2: 90 percent / LiAlH₄ / diethyl ether

3: 63 percent / pyridine / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; acetic acid; In diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja981183g

Reference yield:

1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1(14)-en-2-yl]ethanone (213408-28-7) → thiocarbonic acid O-phenyl ester O-{1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1(14)-en-2-yl]ethyl} ester (213408-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiAlH₄ / diethyl ether

2: 63 percent / pyridine / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; In diethyl ether; dichloromethane;

DOI:10.1021/ja981183g

upstream raw materials:

phenylcarbonochloridothioate

1-[12-(Toluene-4-sulfonyl)-12-aza-bicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]-ethanol

1-[12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-en-2-yl]ethanone

Downstream raw materials:

2-ethyl-12-(toluene-4-sulfonyl)-12-azabicyclo[9.2.1]tetradec-1⁽¹⁴⁾-ene

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