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

Base Information

Chemical Name:(4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-tridecanoic acid methyl ester
CAS No.:865091-30-1
Molecular Formula:C₄₁H₈₀O₁₁
Molecular Weight:749.08
Hs Code.:

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

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

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

There total 1 articles about (4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(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

: 865091-30-1
(4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-tridecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 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: 98 percent / DMAP; DCC / CH₂Cl₂ / 15 h / 20 °C

7.1: 95 percent / Dibal-H / tetrahydrofuran; toluene / 1 h / -78 °C

8.1: (+)-B-methoxy(diisopinocamphenyl)borane / diethyl ether / 2.5 h / 20 °C

8.2: 78 percent / diethyl ether / 2.5 h / -100 °C

9.1: Hunig's base

10.1: 89 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 5 h / Heating

11.1: 100 percent / hydrogen / Pd/C / methanol / 5 h / 20 °C

12.1: 95 percent / NaOMe / 3 h / Heating

13.1: 86 percent / DMAP; ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; dimethylsulfide borane complex; NaH₂PO₄ buffer; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; toluene; acetonitrile; 8.2: Racherla-Brown asymmetric allylation;
DOI:10.1021/ol051483k

Reference yield:

: 865091-30-1
(4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-tridecanoic acid methyl ester

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: (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:: (4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(1''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-tridecanoic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1021/ol051483k

Reference yield:

: 865091-30-1
(4R,10R,13R,2'R,5'R,1''S)-4,10,13-tris(methoxymethoxy)-13-[5'-(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 4 steps

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

1.2: tetrahydrofuran / 2 h / -78 °C

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

3.1: Et₃N; MsCl / CH₂Cl₂ / 0 - 20 °C

3.2: 59.4 mg / DBU / CH₂Cl₂ / 1 h / 20 °C

4.1: 62 percent / TMSBr / CH₂Cl₂ / -78 - 0 °C

With trimethylsilyl bromide; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol051483k