(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Base Information

Chemical Name:(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
CAS No.:150323-18-5
Molecular Formula:C₂₆H₃₈N₂O₃
Molecular Weight:426.599
Hs Code.:

Synonyms:(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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Chemical Property of (3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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Technology Process of (3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

There total 5 articles about (3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 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: 35.0%

: 128019-40-9,149510-73-6,136465-81-1,168899-60-3
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

: 150323-17-4
3R,5S-3-Benzyl-5-mesyloxymethyl-4,5-dihydro-2(3H)-furanon

: 150323-18-5
(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: With potassium carbonate; In xylene; at 140 ℃;
DOI:10.1021/jm00047a001

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 150323-18-5
(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: Et₃N / CH₂Cl₂

5: 35 percent / K₂CO₃ / xylene / 140 °C

With 1H-imidazole; hydrogen fluoride; potassium carbonate; triethylamine; lithium diisopropyl amide; In dichloromethane; acetonitrile; xylene;
DOI:10.1021/jm00047a001

Reference yield:

: 62396-80-9
(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

: 150323-18-5
(3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

2: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

3: Et₃N / CH₂Cl₂

4: 35 percent / K₂CO₃ / xylene / 140 °C

With hydrogen fluoride; potassium carbonate; triethylamine; lithium diisopropyl amide; In dichloromethane; acetonitrile; xylene;
DOI:10.1021/jm00047a001