(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

Base Information

Chemical Name:(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one
CAS No.:1567376-24-2
Molecular Formula:C₄₀H₄₂O₆
Molecular Weight:618.77
Hs Code.:

Synonyms:(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

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Chemical Property of (R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

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Technology Process of (R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

There total 9 articles about (R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-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: 85.0%

: 1567376-23-1
(4R,5E,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-yl acrylate

: 1567376-24-2
(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; Inert atmosphere;
DOI:10.1016/j.tetlet.2013.12.061

Reference yield:

: 1567376-14-0
C₂₇H₃₂O₅

: 1567376-24-2
(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C

2.1: sodium hydride / 3 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

4.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 3 h / -78 °C

5.1: benzene / 2 h / 80 °C

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

7.1: B-chlorodiisopinocampheylborane / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere

7.2: 3 h / -80 °C / Inert atmosphere

8.1: triethylamine; dmap / dichloromethane / Inert atmosphere

9.1: Grubbs catalyst first generation / dichloromethane / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene; 4.1: |Swern Oxidation / 5.1: |Wittig Olefination;
DOI:10.1016/j.tetlet.2013.12.061

Reference yield:

: 1567376-18-4
(2S,3R,4S,5S)-2,3,4,5-tetrakis(benzyloxy)hexanal

: 1567376-24-2
(R)-6-((1E,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: benzene / 2 h / 80 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

3.1: B-chlorodiisopinocampheylborane / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 3 h / -80 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / Inert atmosphere

5.1: Grubbs catalyst first generation / dichloromethane / Inert atmosphere

With Grubbs catalyst first generation; dmap; diisobutylaluminium hydride; triethylamine; B-chlorodiisopinocampheylborane; In diethyl ether; dichloromethane; toluene; benzene; 1.1: |Wittig Olefination;
DOI:10.1016/j.tetlet.2013.12.061