(3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one
• CAS No.: 325740-70-3
• Molecular Formula: C₂₅H₃₉N₃O₅
• Molecular Weight: 461.602

Synonyms:(3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

Chemical Property of (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

There total 43 articles about (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-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: 85.0%

Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-69-0) → (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one (325740-70-3)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium azide; 15-crown-6;

DOI:10.1016/S0040-4039(00)01794-9

Reference yield:

(2S,7R,E)-methyl 2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnon-4-enoate (387353-71-1) → (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one (325740-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide; water / 1,4-dioxane / 24 h / Reflux

1.2: 0 - 5 °C

2.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5

2.2: 14.25 h / 0 - 30 °C

3.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C

4.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C

With hydrogenchloride; N-Bromosuccinimide; sodium azide; phosphoric acid; water; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; 1,1-dichloroethane; water; ethylene glycol;

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one (325740-70-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C

1.2: pH 2

2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere

3.2: -70 - 5 °C

4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C

5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere

5.2: 5.75 h / 0 - 30 °C

6.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C

7.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere

7.2: 12.5 h / 0 - 5 °C

8.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C

8.2: 0.5 h / 0 - 5 °C

9.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5

9.2: 14.25 h / 0 - 30 °C

10.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C

11.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C

With hydrogenchloride; sodium tetrahydroborate; N-chloro-succinimide; N-Bromosuccinimide; sodium azide; lithium hydroxide monohydrate; phosphoric acid; water; dihydrogen peroxide; phosphorus tribromide; magnesium; ethylene dibromide; triphenylphosphine; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,1-dichloroethane; dichloromethane; water; ethylene glycol;

upstream raw materials:

Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

(3S,5S)-5-Hydroxymethyl-3-isopropyl-dihydro-furan-2-one

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-isopropyl-dihydro-furan-2-one

Downstream raw materials:

(2S,4S,5R,7S)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-isopropylnonanamide

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

(2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide

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