(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

Base Information

Chemical Name:(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester
CAS No.:865091-46-9
Molecular Formula:C₃₉H₇₆O₁₀
Molecular Weight:705.026
Hs Code.:

(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

Synonyms:(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

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Chemical Property of (4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

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Technology Process of (4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

There total 1 articles about (4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester 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:

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

: 865091-46-9
(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / pyridine / CHCl₃ / 12 h / 0 °C

2.1: BH₃*DMS / tetrahydrofuran / 0 - 20 °C

2.2: 79 percent / imidazole / dimethylformamide / 15 h / 20 °C

3.1: tetrahydrofuran / -78 - 20 °C

3.2: 90 percent / ethyldiisopropylamine; DMAP; tetra-n-butylammonium iodide / CH₂Cl₂ / 96 h

4.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

5.1: 60 percent / TEMPO; NaClO₂; NaH₂PO₄ buffer / acetonitrile; H₂O / 20 h / 45 °C / pH 6.6

6.1: 83 percent / DMAP; DCC

7.1: 89 percent / first generation Grubbs' catalyst / CH₂Cl₂ / 18 h / Heating

8.1: 100 percent / hydrogen / Pd/C / ethyl acetate / 18 h

9.1: 100 percent / NaOMe / 5 h / Heating

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; dimethylsulfide borane complex; NaH₂PO₄ buffer; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; dicyclohexyl-carbodiimide; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; acetonitrile;
DOI:10.1021/ol051483k

Reference yield:

: 865091-46-9
(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

: (10R,13R)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-4,10,13-tris-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 96 percent / DMAP; ethyldiisopropylamine; TBAI / CH₂Cl₂ / 96 h

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 2 h / -78 °C

With dmap; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051483k

Reference yield:

: 865091-46-9
(4R,10R,13R)-10-Hydroxy-4,13-bis-methoxymethoxy-13-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-tridecanoic acid methyl ester

: 170902-34-8
(5S,2'R,8'R,11'R,2''R,5''R,1'''S)-5-methyl-3-{2',8',11'-trihydroxy-11'-[5''-(1'''-hydroxy-pentadecyl)-tetrahydro-furan-2''-yl]-undecyl}-5H-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / DMAP; ethyldiisopropylamine; TBAI / CH₂Cl₂ / 96 h

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 2 h / -78 °C

3.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

4.1: Et₃N; MsCl / CH₂Cl₂ / 0 - 20 °C

4.2: 59.4 mg / DBU / CH₂Cl₂ / 1 h / 20 °C

5.1: 62 percent / TMSBr / CH₂Cl₂ / -78 - 0 °C

With dmap; trimethylsilyl bromide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051483k