<4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone

Base Information

• Chemical Name: <4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone
• CAS No.: 121441-80-3
• Molecular Formula: C₃₄H₄₁NO₅
• Molecular Weight: 543.703

Synonyms:<4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone

Chemical Property of <4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone

Chemical Property:

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Safty Information:

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Technology Process of <4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone

There total 2 articles about <4R-<3(2R^*,3S^*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone 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:

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → <4R-<3(2R*,3S*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone (121441-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 26 g / 10percent aq. NaOH / diethyl ether; toluene / 2.5 h / Ambient temperature

2: 1.) n-butyllithium / 1.) THF, -40 deg C, 30 min, 2.) THF, -74 deg C, 30 min

3: 1.) di-n-butylboryl triflate, i-Pr₂EtN / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 0.5 h, b) 0 deg C, 20 min

With sodium hydroxide; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; toluene;

DOI:10.1021/jo00275a045

Reference yield:

2-(8-phenyloctyl) benzaldehyde (96964-45-3) + <4R,5S>-3-<1-oxo-2-(methoxy)ethyl>-4-methyl-5-phenyl-2-oxazolidinone (121441-79-0) → <4R-<3(2R*,3S*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone (121441-80-3)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 0.5 h, b) 0 deg C, 20 min;

DOI:10.1021/jo00275a045

Reference yield: 70.0%

Methyl 3-mercaptopropionate (2935-90-2) + <4R-<3(2R*,3S*),4α,5α>>-3-<3-hydroxy-2-methoxy-1-oxo-3-<2-(8-phenyloctyl)phenyl>propyl>-4-methyl-5-phenyl-2-oxozolidinone (121441-80-3) → <4R-<3(2S*,3S*),4α,5α>>-methyl 2-<<2-methoxy-3-(4-methyl-2-oxo-5-phenyl-3-oxazolidinyl)-3-oxo-1-<2-(8-phenyloctyl)phenyl>propyl>thio>propanoate (121441-86-9)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 18h;

DOI:10.1021/jo00275a045

upstream raw materials:

2-(8-phenyloctyl) benzaldehyde

<4R,5S>-3-<1-oxo-2-(methoxy)ethyl>-4-methyl-5-phenyl-2-oxazolidinone

(1S,2R)-(+)-norphedrine

Downstream raw materials:

<4R-<3(2S^*,3S^*),4α,5α>>-methyl 2-<<2-methoxy-3-(4-methyl-2-oxo-5-phenyl-3-oxazolidinyl)-3-oxo-1-<2-(8-phenyloctyl)phenyl>propyl>thio>propanoate

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