2(3H)-Furanone, 5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]dihydro-3-(1-methylethyl)-, (3S,5S)-

Base Information

• Chemical Name: 2(3H)-Furanone, 5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]dihydro-3-(1-methylethyl)-, (3S,5S)-
• CAS No.: 173154-03-5
• Molecular Formula: C₁₄H₂₅N₃O₃
• Molecular Weight: 283.371
• Mol file: 173154-03-5.mol

Synonyms:(3S,5S)-5-((1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one;(3S,5S,1'S,3'S)-5-(1'-azido-3'-hydroxymethyl-4'-methylpentyl)-3-isopropyl-dihydrofuran-2-one;

Chemical Property of 2(3H)-Furanone, 5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]dihydro-3-(1-methylethyl)-, (3S,5S)-

Chemical Property:

• PSA: 96.28000
• LogP: 2.36036

Purity/Quality:

98%min ^*data from raw suppliers

(3S,5S)-5-((1S,3S)-1-Azido-3-(hydroxymethyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(3H)-Furanone, 5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]dihydro-3-(1-methylethyl)-, (3S,5S)-

There total 4 articles about 2(3H)-Furanone, 5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]dihydro-3-(1-methylethyl)-, (3S,5S)- 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: 94.0%

(2S,2'S,2S,4S)-2-[2-azido-2'-(4-isopropyl-5-oxo-tetrahydrofuran-2-yl)-ethyl]-3-methylbutyric acid (173153-98-5) → (3S,5S)-5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-isopropyldihydrofuran-2(3H)-one (173154-03-5)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 48h;

DOI:10.1055/s-0034-1378616

Reference yield:

(2S,2'S,2S,4S)-2-[2-azido-2'-(4-isopropyl-5-oxo-tetrahydrofuran-2-yl)-ethyl]-3-methylbutyric acid (173153-98-5) + sodium methylate (124-41-4) → (3S,5S)-5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-isopropyldihydrofuran-2(3H)-one (173154-03-5)

Guidance literature:

(2S,2'S,2"S,4"S)-2-[2-azido-2'-(4"-isopropyl-5"-oxo-tetrahydrofuran-2"-yl)-ethyl]-3-methylbutyric acid; With triethylamine; methyl chloroformate; In tetrahydrofuran; at -10 - 0 ℃; for 3h;

sodium methylate; With sodium tetrahydroborate; In tetrahydrofuran; at -20 - 5 ℃;

Reference yield:

(S)-3-((2S,4S)-4-azido-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)butanoyl)-4-benzyloxazolidin-2-one (173154-01-3) → (3S,5S)-5-[(1S,3S)-1-azido-3-(hydroxymethyl)-4-methylpentyl]-3-isopropyldihydrofuran-2(3H)-one (173154-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 0 - 20 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 20 °C

With lithium hydroxide monohydrate; dimethylsulfide borane complex; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1055/s-0034-1378616

upstream raw materials:

(2S,2'S,2S,4S)-2-[2-azido-2'-(4-isopropyl-5-oxo-tetrahydrofuran-2-yl)-ethyl]-3-methylbutyric acid

sodium methylate

(S)-3-((2S,4S)-4-azido-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)butanoyl)-4-benzyloxazolidin-2-one

Downstream raw materials:

(2S,4S)-4-azido-2-isopropyl-4-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]butanal

(3S,5S)-5-((1S,3S)-1-Azido-3-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

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