(1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane

Base Information

• Chemical Name: (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane
• CAS No.: 445482-91-7
• Molecular Formula: C₃₁H₃₅O₂PS
• Molecular Weight: 502.657

Synonyms:(1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane

Chemical Property of (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane

Chemical Property:

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Technology Process of (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane

There total 3 articles about (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.0^3,8]undecane 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: 91.0%

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) + (2-formylphenyl)[di(m-tolyl)]phosphine oxide (445482-88-2) → (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.03,8]undecane (445482-91-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 6h; Heating;

DOI:10.1021/jo0201474

Reference yield:

bis(3-methylphenyl)phosphine oxide (145290-34-2) → (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.03,8]undecane (445482-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; i-Pr₂NEt / dimethylsulfoxide / 20 h / 100 °C

2: 91 percent / p-TsOH*H₂O / benzene / 6 h / Heating

With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; benzene;

DOI:10.1021/jo0201474

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → (1R,3R,5R,8S)-11,11-dimethyl-4-oxa-5-[2-di(m-tolyl)phosphinyl]phenyl-6-thiatricyclo[6.2.1.03,8]undecane (445482-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; i-Pr₂NEt / dimethylsulfoxide / 20 h / 100 °C

2: 91 percent / p-TsOH*H₂O / benzene / 6 h / Heating

With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; benzene;

DOI:10.1021/jo0201474

upstream raw materials:

(1S,2R,4R)-(-)-10-mercaptoisoboneol

(2-formylphenyl)[di(m-tolyl)]phosphine oxide

bis(3-methylphenyl)phosphine oxide

ortho-bromobenzaldehyde

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