(S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one
• CAS No.: 149836-92-0
• Molecular Formula: C₂₄H₃₅NO₄Si
• Molecular Weight: 429.632
• Mol file: 149836-92-0.mol

Synonyms:(S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one

Chemical Property of (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one

There total 2 articles about (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one 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:

(S)-2-(benzyloxy)propanal (81445-44-5) → (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one (149836-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 45 min, -78 deg C --> rt, 2-4 h, rt, 8 h

2: 1.) octacarbonyldicobalt, 2.) Bu₂BOTf, diisopropylethylamine, 3.) ceric ammonium nitrate / 1) Et₂O, 40 min; 2) CH₂Cl₂, -78 deg C, 30 min, 0 deg C, 30 min; 3) acetone, rt, 40 min

With n-butyllithium; dicobalt octacarbonyl; ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;

DOI:10.1021/jo970288j

Reference yield:

C17H32BNO3 (87758-64-3) + 4(S)-benzyloxy-3-methoxy-1-(trimethylsilyl)pentyne, hexacarbonyldicobal complex → (S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one (149836-92-0)

Guidance literature:

With ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 20 min, rt, 20 min, 2.) acetone, rt;

DOI:10.1021/jo952092u

Reference yield: 86.0%

(S)-3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-isopropyl-oxazolidin-2-one (149836-92-0) → (2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid (145071-98-3)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 18h; Ambient temperature;

DOI:10.1021/jo952092u

upstream raw materials:

C₁₇H₃₂BNO₃

(S)-2-(benzyloxy)propanal

Downstream raw materials:

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid

2-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-methyl-2-methylene-5-oxo-pyrrolidin-1-yl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

(2S,3S)-2-((R)-1-Amino-ethyl)-3-benzyloxy-butyric acid