(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

Base Information

Chemical Name:(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione
CAS No.:782472-61-1
Molecular Formula:C₃₄H₄₈O₆
Molecular Weight:552.752
Hs Code.:

Synonyms:(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

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Chemical Property of (3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

Chemical Property:

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Technology Process of (3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

There total 29 articles about (3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione 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: 61.0%

: 782472-42-8
(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-((R)-2-benzyloxy-3-carboxy-propyl)-hexyl ester

: 782472-61-1
(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; toluene; at 90 ℃; for 24h;
DOI:10.1016/j.tetlet.2004.08.052

Reference yield: 52.0%

: (3R,5R)-3-(benzyloxy)-5-hydroxydecanoic acid

: 782472-61-1
(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

Guidance literature:: (3R,5R)-3-(benzyloxy)-5-hydroxydecanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With dmap; In toluene; at 90 - 100 ℃; for 10h;
DOI:10.1007/s00706-014-1272-z

Reference yield:

: 782472-49-5
(R)-3-(4-Methoxy-benzyloxy)-octanal

: 782472-61-1
(3R,5R,9R,11R)-3,9-bis(benzyloxy)-5,11-dipentylcyclododecane-1,7-dione

Guidance literature:: Multi-step reaction with 13 steps

1: 85 percent / benzene / 2 h / Heating

2: 79 percent / DIBAL-H / CH₂Cl₂ / 3 h / 20 °C

3: 83 percent / cumene hydroperoxide; (-)-DIPT; Ti(Oi-Pr)4 / CH₂Cl₂ / 3 h / -20 °C

4: 80 percent / NaAlH₂(OCH₂CH₂OMe)2 / tetrahydrofuran / 5 h / 0 °C

5: 84 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

6: 78 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

7: 89 percent / TBAF / CH₂Cl₂ / 10 h / 20 °C

8: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

9: 83 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 10 h / 0 - 20 °C

10: 66 percent / 2,4,6-trichlorobenzoyl cloride; Et₃N; DMAP / tetrahydrofuran; toluene / 20 h / 20 °C

11: 69 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

12: 68 percent / DBN / benzene / 12 h / 20 °C

13: 61 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 24 h / 90 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium chlorite; oxalyl dichloride; Cumene hydroperoxide; 2,6-dichloro-benzonitrile; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 3: Sharpless asymmetric epoxidation / 8: Swern oxidation;
DOI:10.1016/j.tetlet.2004.08.052