406684-20-6

Basic information

• Product Name: 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole
• Synonyms: 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole
• CAS NO: 406684-20-6
• Molecular Weight: 416.544
• Mol File: 406684-20-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole(406684-20-6)
• EPA Substance Registry System: 5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole(406684-20-6)

Safety Data

• Hazardous Substances Data: 406684-20-6(Hazardous Substances Data)

Upstream product

• 934623-86-6 tert-butyl-((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-enyloxy)dimethylsilane 
• 393530-60-4 1-[(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-2-pyranyl]-1-ethanone 
• 863895-02-7 (1S)-1-[(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-2-pyranyl]ethan-1-ol 
• 902769-00-0 C₉H₂₀OSi 
• 96481-55-9 2-methylpent-1-en-3-ol 
• 393530-64-8 [2R,6R,2(2'S,3'E)]-2-(1-hydroxy-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran 
• 130856-15-4 (+)-(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl carboxylic acid 
• 380355-90-8 ((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)methanol 
• 1235459-89-8 (2R,6R)-2-(benzyloxymethyl)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran 
• 406684-16-0 (S)-4-Benzyl-3-[(R)-2-((R)-1-ethyl-2-methyl-allyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 406684-17-1 (S)-4-Benzyl-3-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-carbonyl)-oxazolidin-2-one 
• 406684-15-9 (S)-4-Benzyl-3-[2-((R)-1-ethyl-2-methyl-allyloxy)-acetyl]-oxazolidin-2-one 
• 406684-19-3 (S)-4-Benzyloxy-1-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-butan-1-one 
• 406684-14-8 ((R)-1-Ethyl-2-methyl-allyloxy)-acetic acid 

Downstream Products

• 130799-17-6 methyl 5β,6α-dibenzyloxypolyangioate 
• 58857-02-6 (+)-ambruticin S 

Relevant articles and documents

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Total synthesis of Jerangolid A

(Figure Presented) The first total synthesis of the antifungal polyketide jerangolid A has been accomplished. Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyz