(2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

Base Information

• Chemical Name: (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid
• CAS No.: 189246-66-0
• Molecular Formula: C₂₈H₄₅NO₆
• Molecular Weight: 491.668
• Mol file: 189246-66-0.mol

Synonyms:(2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

Chemical Property of (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

There total 29 articles about (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid 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: 58.0%

(1'S,4'S,16S,17S,18R)-17-benzyloxy-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-16,18-dihydroxyoctadec-14-ene-7-one (189246-65-9) → (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid (189246-66-0)

Guidance literature:

(1'S,4'S,16S,17S,18R)-17-benzyloxy-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-16,18-dihydroxyoctadec-14-ene-7-one; With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1h;

With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

(3RS)-ethyl-3-hydroxynonanethioate (189246-52-4) → (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid (189246-66-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: diisopropylethylamine / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

5.1: H₂ / Pd/C / ethanol / 20 h / 760 Torr

6.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 100 percent / HCl / methanol / 3 h / 50 °C

8.1: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

9.1: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

10.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

11.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

12.1: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

13.1: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

14.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

14.2: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

14.3: 91 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

15.1: 78 percent / formic acid / diethyl ether / 0.5 h / 0 °C

16.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

17.1: 83 percent / n-BuLi; SnCl₂ / tetrahydrofuran; hexane / 3.5 h / -78 - 0 °C

18.1: 94 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

19.1: TsOH / tetrahydrofuran / 1 h / 20 °C

19.2: 58 percent / aq. NaOH / methanol / 0.5 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Etherification / 2.1: Reduction / 3.1: Bromination / 4.1: Addition / 5.1: Reduction / 6.1: Bromination / 7.1: Elimination / 8.1: Etherification / 9.1: Addition / 10.1: Elimination / 11.1: Swern oxidation / 12.1: Elimination / 13.1: Etherification / 14.1: Etherification / 14.2: Reduction / 14.3: Etherification / 15.1: Elimination / 16.1: Swern oxidation / 17.1: Condensation / 18.1: Elimination / 19.1: Hydrolysis / 19.2: Hydrolysis;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

1-bromo-3-(methoxymethoxy)nonane → (2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid (189246-66-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

2.1: H₂ / Pd/C / ethanol / 20 h / 760 Torr

3.1: CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 100 percent / HCl / methanol / 3 h / 50 °C

5.1: 97 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 20 °C

6.1: 89 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

7.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

8.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

9.1: 100 percent / HCl / tetrahydrofuran / 0.5 h / 20 °C

10.1: 94 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

11.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

11.2: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

11.3: 91 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

12.1: 78 percent / formic acid / diethyl ether / 0.5 h / 0 °C

13.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

14.1: 83 percent / n-BuLi; SnCl₂ / tetrahydrofuran; hexane / 3.5 h / -78 - 0 °C

15.1: 94 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

16.1: TsOH / tetrahydrofuran / 1 h / 20 °C

16.2: 58 percent / aq. NaOH / methanol / 0.5 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Addition / 2.1: Reduction / 3.1: Bromination / 4.1: Elimination / 5.1: Etherification / 6.1: Addition / 7.1: Elimination / 8.1: Swern oxidation / 9.1: Elimination / 10.1: Etherification / 11.1: Etherification / 11.2: Reduction / 11.3: Etherification / 12.1: Elimination / 13.1: Swern oxidation / 14.1: Condensation / 15.1: Elimination / 16.1: Hydrolysis / 16.2: Hydrolysis;

DOI:10.1016/S0040-4020(98)00484-0

upstream raw materials:

(1'S,4'S,16S,17S,18R)-17-benzyloxy-18-(3',6'-diethoxy-1',4'-dimethyl-4'H-2',5'-diazyl)-16,18-dihydroxyoctadec-14-ene-7-one

heptanal

(7RS)-1-bromo-7-tridecanol

1-bromo-7-methoxymethoxytridecane

Downstream raw materials:

sphingofungin F

Refernces

• 1、 Kobayashi, Shu. "Catalytic asymmetric syntheses of antifungal sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT)". . p. 908 - 919. Retrieved 2007/10/03.