(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

Base Information

Chemical Name:(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one
CAS No.:865091-29-8
Molecular Formula:C₃₈H₇₂O₉
Molecular Weight:672.984
Hs Code.:

(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

Synonyms:(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

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Chemical Property of (5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

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Technology Process of (5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

There total 1 articles about (5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-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:

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

: 865091-29-8
(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

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: 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

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

Reference yield:

: 865091-29-8
(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

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

: 865091-32-3
(5R,11R)-3-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-5-methoxymethoxy-11-{(R)-3-methoxymethoxy-3-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-propyl}-oxacycloundecan-2-one

Guidance literature:: (5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one; 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:

: 865091-29-8
(5R,11R,3'R,2''R,5''R,1'''S)-5-methoxymethoxy-11-{3-methoxymethoxy-3-[5'-(1'''-methoxymethoxy-pentadecyl)-tetrahydro-furan-2'-yl]-propyl}-oxacycloundecan-2-one

: (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 3 steps

1.1: 100 percent / NaOMe / 5 h / Heating

2.1: 96 percent / DMAP; ethyldiisopropylamine; TBAI / CH₂Cl₂ / 96 h

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

3.2: tetrahydrofuran / 2 h / -78 °C

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