<3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 124356-84-9
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 124356-84-9.mol

Synonyms:<3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone

There total 8 articles about <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone 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:

2-methylpropenal (78-85-3,25120-30-3) + (S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0) → <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone (124356-84-9)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, -20 deg C, 1 h, 2) -78 deg C, 30 min;

DOI:10.1021/jo00305a006

Reference yield:

2-methylpropenal (78-85-3,25120-30-3) + (S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0) → <3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone (124356-84-9) + (2S,4S,5S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4,6-trimethyl-hept-6-ene-1,3-dione (124440-00-2)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1.) -20 deg C, 1 h, CH₂Cl₂, 2.) -78 deg C, 30 min;

DOI:10.1021/ja00158a056

Reference yield:

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → <<3-(2R,4R,5S),4R>-3-(5-Hydroxy-2,4,6-trimethyl-1,3-dioxo-hept-6-enyl)-4-(phenylmethyl)>-2-oxazolidinone (124356-84-9,124440-00-2,141505-93-3,141505-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) dibutylboron triflate, triethylamine / 1) CH₂Cl₂

2: 95 percent / DMSO, triethylamine, sulfurtrioxide-pyridine complex / CH₂Cl₂ / 0 °C

3: 1) (c-hex)2BCl, EtNMe₂ / 1) Et₂O, 0 deg C, 1 h, 2) -78 deg C, 3 h, 3) -78 to -20 deg C, 2 h

With N,N-dimethyl-ethanamine; di-n-butylboryl trifluoromethanesulfonate; dicyclohexylboron chloride; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)88879-7

upstream raw materials:

2-methylpropenal

(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

(3R)-3-propionyl-4-benzyloxazolidin-2-one

Downstream raw materials:

[[3-(2S,3R,4S,5R)-4S]-3-(3,5-dihydroxy-2,4,6-trimethyl-1-oxohept-6-enyl)-4-(phenylmethyl)]-2-oxazolidinone

<3(2S,4R,5S),6S>-3-<1-oxo-2-<2,2,5-trimethyl-4-(1-methylethenyl)-1,3-dioxan-6-yl>propyl>-4-(phenylmethyl)-2-oxazolidinone

(4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

(4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-methoxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone