(S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate

Base Information

• Chemical Name: (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate
• CAS No.: 1599436-47-1
• Molecular Formula: C₂₈H₄₃NO₇
• Molecular Weight: 505.652
• Mol file: 1599436-47-1.mol

Synonyms:(S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate

Chemical Property of (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate

There total 6 articles about (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate 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: 83.0%

(4S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-3-hydroxy-2,2,6-trimethylheptanoate (1599436-52-8) → (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate (1599436-47-1)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ol500484f

Reference yield:

tert-butoxycarbonyl-L-leucinal (58521-45-2) → (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate (1599436-47-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: montmorrolonite K₁₀ / water; dichloromethane / 20 °C / Inert atmosphere

2.1: sodium sulfate; toluene-4-sulfonic acid / dichloromethane / 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; dichloromethane / 18 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

4.1: sodium dihydrogen phosphate monohydrate; sodium chlorite; 2-methyl-but-2-ene / tert-butyl alcohol; water / 18 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine; 2-methyl-6-nitrobenzoic anhydride / 0.25 h / 20 °C / Inert atmosphere

5.2: 40 h / 20 °C / Inert atmosphere

6.1: hydrogenchloride / ethyl acetate; water / 18 h / 20 °C / Inert atmosphere

7.1: pyridine; Dess-Martin periodane / dichloromethane / 14 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium chlorite; osmium(VIII) oxide; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; 2-methyl-6-nitrobenzoic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; sodium sulfate; triethylamine; In dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/ol500484f

Reference yield:

C18H33NO4 (1599436-56-2) → (S)-(S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl 4-((tert-butoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate (1599436-47-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium dihydrogen phosphate monohydrate; sodium chlorite; 2-methyl-but-2-ene / tert-butyl alcohol; water / 18 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine; 2-methyl-6-nitrobenzoic anhydride / 0.25 h / 20 °C / Inert atmosphere

2.2: 40 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / ethyl acetate; water / 18 h / 20 °C / Inert atmosphere

4.1: pyridine; Dess-Martin periodane / dichloromethane / 14 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; 2-methyl-6-nitrobenzoic anhydride; Dess-Martin periodane; triethylamine; In dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/ol500484f

upstream raw materials:

tert-butoxycarbonyl-L-leucinal

tert-butyl ((4S,5S)-5-hydroxy-2,6,6-trimethyloct-7-en-4-yl)-carbamate

(4S)-tert-butyl 4-isobutyl-2,2-dimethyl-5-(2-methylbut-3-en-2-yl)oxazolidine-3-carboxylate

C₁₈H₃₃NO₄