<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

Base Information

• Chemical Name: <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
• CAS No.: 121441-86-9
• Molecular Formula: C₃₈H₄₇NO₆S
• Molecular Weight: 645.86

Synonyms:<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

Chemical Property of <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

Chemical Property:

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Technology Process of <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

There total 3 articles about <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 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: 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

Reference yield:

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → <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:

Multi-step reaction with 4 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

4: 70 percent / trifluoroacetic acid / 18 h / 0 °C

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

DOI:10.1021/jo00275a045

Reference yield:

<4R,5S>-3-<1-oxo-2-(methoxy)ethyl>-4-methyl-5-phenyl-2-oxazolidinone (121441-79-0) → <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:

Multi-step reaction with 2 steps

1: 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

2: 70 percent / trifluoroacetic acid / 18 h / 0 °C

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;

DOI:10.1021/jo00275a045

upstream raw materials:

Methyl 3-mercaptopropionate

<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

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

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

Downstream raw materials:

*,R^*)>-β-<(2-carboxyethyl)thio>-α-methoxy-2-(8-phenyloctyl)benzenepropanoic acid

*,R^*)>-methyl α-methoxy-β-<(3-methoxy-3-oxopropyl)thio>-2-(8-phenyloctyl)benzenepropanoate

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