(4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester

Base Information

• Chemical Name: (4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester
• CAS No.: 1054649-80-7
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 1054649-80-7.mol

Synonyms:(4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester

Chemical Property of (4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester

There total 1 articles about (4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester 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:

ethyl (4E)-8-benzyloxy-4-enoctanoate (181803-05-4) → (4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester (1054649-80-7)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1021/jo961286m

Reference yield:

(4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester (1054649-80-7) → (R)-5-[(Z)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-7-((4R,5R)-5-decyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enyl]-dihydro-furan-2-one (182072-80-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH

2: TsOH / CH₂Cl₂ / 1 h

3: imidazole / dimethylformamide / 16 h / Ambient temperature

4: H₂ / Pd/C (10percent) / methanol; propionic acid / 24 h

5: PCC, celite / CH₂Cl₂ / 2 h

6: 1.) KN(SiMe₃)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h

With 1H-imidazole; hydrogenchloride; potassium hydroxide; Celite; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane; propionic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo961286m

Reference yield:

(4S,5S)-8-Benzyloxy-4,5-dihydroxy-octanoic acid ethyl ester (1054649-80-7) → 4-Nitro-benzoic acid (S)-3-((4R,5R)-5-decyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-((2S,5S,2'R)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-propyl ester

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH

2: TsOH / CH₂Cl₂ / 1 h

3: imidazole / dimethylformamide / 16 h / Ambient temperature

4: H₂ / Pd/C (10percent) / methanol; propionic acid / 24 h

5: PCC, celite / CH₂Cl₂ / 2 h

6: 1.) KN(SiMe₃)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h

7: Bu₄NF / dimethylformamide / 2 h / Ambient temperature

8: 1.) Re₂O₇, lutidine, 2.) TsOH / 1.) CH₂Cl₂, 4 h, 2.) dimethoxypropane, acetone, 1 h

9: PPH₃, DEAD / benzene / 16 h

With 1H-imidazole; hydrogenchloride; potassium hydroxide; Celite; lutidine; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; rhenium(VII) oxide; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; palladium on activated charcoal; In methanol; dichloromethane; propionic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo961286m

upstream raw materials:

ethyl (4E)-8-benzyloxy-4-enoctanoate

Downstream raw materials:

(S)-5-((S)-4-Benzyloxy-1-hydroxy-butyl)-dihydro-furan-2-one

(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde

(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde