(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 858666-74-7
• Molecular Formula: C₂₅H₃₁NO₅
• Molecular Weight: 425.525
• Mol file: 858666-74-7.mol

Synonyms:(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property of (2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

There total 1 articles about (2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-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: 90.0%

5-benzyloxy-1-pentanal (78999-24-3) + (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) → (2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one (858666-74-7)

Guidance literature:

With titanium tetrachloride; (-)-sparteine; In dichloromethane;

DOI:10.1021/ol0507975

Reference yield: 87.0%

(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one (858666-74-7) → (2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol (786668-23-3)

Guidance literature:

With lithium borohydride; In tetrahydrofuran;

DOI:10.1021/ol0507975

Reference yield:

(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one (858666-74-7) → Methanesulfonic acid (E)-3-{(2S,5R,7S)-7-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-allyl ester

Guidance literature:

Multi-step reaction with 14 steps

1.1: 87 percent / LiBH₄ / tetrahydrofuran / 0.08 h / 20 °C

2.1: 77 percent / imidazole / CH₂Cl₂ / 20 h / 20 °C

3.1: 95 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / dimethylformamide / 20 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / methanol

5.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

7.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

8.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

9.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

10.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

11.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

12.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

13.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

14.1: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; diisobutylaluminum hydride; hydrogen; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 12.1: Wittig olefination;

DOI:10.1039/b600951d

upstream raw materials:

5-benzyloxy-1-pentanal

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

Downstream raw materials:

(2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol

(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-formyl-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

(1'E,2S,5R,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(3'-hydroxy-1'-propenyl)-1,6-dioxaspiro[4.5]decane