(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate

Base Information

• Chemical Name: (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate
• CAS No.: 314031-12-4
• Molecular Formula: C₂₈H₄₆N₂O₆
• Molecular Weight: 506.683
• Mol file: 314031-12-4.mol

Synonyms:(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate

Chemical Property of (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate

There total 11 articles about (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate 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: 94.0%

(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate (314031-10-2) → (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate (314031-12-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00772-9

Reference yield:

Octanal (124-13-0) → (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate (314031-12-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / Et₃N; n-Bu₂BOTf / CH₂Cl₂ / 3 h / -78 - 20 °C

2: 88 percent / pyridinium-p-toluenesulfonate / CH₂Cl₂ / 20 °C

3: 84 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 3.5 h / 0 - 20 °C

4: 70 percent / diisopropylethylamine; [benzotriazol-1-yloxy-tris(dimethylamino)phosphonium]PF₆ / acetonitrile / 2 h / 20 °C

5: 90 percent / p-TsOH / methanol / 2 h / 20 °C

6: 0.48 g / 4-dimethylaminopyridine / benzene / 2 h / 20 °C

7: 78 percent / Me₃SiBr / CH₂Cl₂ / 4 h / -30 - 0 °C

8: H₂ / Pd(OH)2 / methanol / 20 °C

9: 94 percent / CF₃COOH / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium hydroxide; trimethylsilyl bromide; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene; 1: Condensation / 2: Addition / 3: amide cleavage / 4: Condensation / 5: ketal cleavage / 6: Esterification / 7: ketal cleavage / 8: Hydrogenolysis / 9: carbamate cleavage;

DOI:10.1016/S0040-4020(00)00772-9

Reference yield:

(2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoic acid (174623-92-8) → (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate (314031-12-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / diisopropylethylamine; [benzotriazol-1-yloxy-tris(dimethylamino)phosphonium]PF₆ / acetonitrile / 2 h / 20 °C

2: 90 percent / p-TsOH / methanol / 2 h / 20 °C

3: 0.48 g / 4-dimethylaminopyridine / benzene / 2 h / 20 °C

4: 78 percent / Me₃SiBr / CH₂Cl₂ / 4 h / -30 - 0 °C

5: H₂ / Pd(OH)2 / methanol / 20 °C

6: 94 percent / CF₃COOH / CH₂Cl₂ / 2 h / 20 °C

With dmap; trimethylsilyl bromide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; acetonitrile; benzene; 1: Condensation / 2: ketal cleavage / 3: Esterification / 4: ketal cleavage / 5: Hydrogenolysis / 6: carbamate cleavage;

DOI:10.1016/S0040-4020(00)00772-9

upstream raw materials:

(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]amino}-1-methyl-2-oxoethyl)octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate

Octanal

(2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoic acid

(4S)-3<(2'S,3'R)-2'-methyl-3'-hydroxydecanoyl>-4-phenylmethyl-2-oxazolidinone