(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester

Base Information

Chemical Name:(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester
CAS No.:865091-40-3
Molecular Formula:C₃₈H₇₀O₈
Molecular Weight:654.969
Hs Code.:

Synonyms:(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester

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Chemical Property of (1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester

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Technology Process of (1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester

There total 1 articles about (1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl 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

: 865091-40-3
(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl ester

Guidance literature:: Multi-step reaction with 8 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

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; dimethylsulfide borane complex; NaH₂PO₄ buffer; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; toluene; acetonitrile; 8.2: Racherla-Brown asymmetric allylation;
DOI:10.1021/ol051483k

Reference yield:

: 865091-40-3
(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl 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 6 steps

1.1: Hunig's base

2.1: 89 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 5 h / Heating

3.1: 100 percent / hydrogen / Pd/C / methanol / 5 h / 20 °C

4.1: 95 percent / NaOMe / 3 h / Heating

5.1: 86 percent / DMAP; ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

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

6.2: tetrahydrofuran / 2 h / -78 °C

With dmap; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol051483k

Reference yield:

: 865091-40-3
(1R,4S,2'R,5'R,4''R,1'''S)-4''-methoxymethoxy-oct-7-enoic acid 4-hydroxy-1-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-hept-6-enyl 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 9 steps

1.1: Hunig's base

2.1: 89 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 5 h / Heating

3.1: 100 percent / hydrogen / Pd/C / methanol / 5 h / 20 °C

4.1: 95 percent / NaOMe / 3 h / Heating

5.1: 86 percent / DMAP; ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

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

6.2: tetrahydrofuran / 2 h / -78 °C

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

8.1: Et₃N; MsCl / CH₂Cl₂ / 0 - 20 °C

8.2: 59.4 mg / DBU / CH₂Cl₂ / 1 h / 20 °C

9.1: 62 percent / TMSBr / CH₂Cl₂ / -78 - 0 °C

With dmap; trimethylsilyl bromide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol051483k