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

Base Information

• Chemical Name: (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate
• CAS No.: 314030-97-2
• Molecular Formula: C₄₀H₅₉NO₉
• Molecular Weight: 697.91
• Mol file: 314030-97-2.mol

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

Chemical Property of (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-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-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate

There total 27 articles about (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-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: 77.0%

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester (676525-98-7) → (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate (314030-97-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

Reference yield:

((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester (99113-30-1) → (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate (314030-97-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / imidazole / dimethylformamide / 10 h / 20 °C

2.1: 98 percent / NaH / dimethylformamide / 12 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

3.2: NaOOH / 3 h / 50 °C

3.3: TEMPO; NaOCl; NaClO₂ / acetonitrile; aq. phosphate buffer / 4.5 h / 20 °C / pH 6.8

4.1: 89 percent / EDCI; DMAP / CH₂Cl₂ / 8 h / 40 °C

5.1: H₂ / Pd(OH)2 / ethanol / 1 h / 20 °C / 760 Torr

6.1: 97 percent / EDCI; DMAP / CH₂Cl₂ / 12 h / 20 °C

7.1: 77 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(2S,3R)-3-Hydroxy-2-methyl-pent-4-enoic acid methyl ester (101249-11-0,145362-91-0,145362-93-2) → (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate (314030-97-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 42 percent / Candida antarctica (fraction B) / toluene / 60 h / 20 °C

2: 85 percent / K₂CO₃ / methanol / 1 h / 20 °C

3: 71 percent / chiral ruthenium complex / CH₂Cl₂ / 12 h / 20 °C

4: 82 percent / H₂ / Pd/C / ethanol / 2 h / 760 Torr

5: aq. NaOH / methanol / 5 h / 20 °C

6: Cs₂CO₃ / dimethylformamide / 12 h / 20 °C

7: 89 percent / EDCI; DMAP / CH₂Cl₂ / 8 h / 40 °C

8: H₂ / Pd(OH)2 / ethanol / 1 h / 20 °C / 760 Torr

9: 97 percent / EDCI; DMAP / CH₂Cl₂ / 12 h / 20 °C

10: 77 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

With dmap; sodium hydroxide; Candida antarctica (fraction B); tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester

(2S,3R)-3-Hydroxy-2-methyl-pent-4-enoic acid methyl ester

Methyl (2S,3R)-3-hydroxy-2-methyldecanoate

Downstream raw materials:

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

(-)-hapalosin

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