(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

Base Information

Chemical Name:(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate
CAS No.:1345135-19-4
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

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Chemical Property of (2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

Chemical Property:

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Technology Process of (2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

There total 1 articles about (2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate 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: 98.0%

: 83541-13-3
(R)-(+)-6-(benzyloxy)-4-methylhexanal

: 21382-82-1
(carbethoxyethylidene)triphenylphosphorane

: 1345135-19-4
(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

Guidance literature:: In benzene; for 4h; Reflux;
DOI:10.1016/j.tet.2011.09.066

Reference yield: 90.0%

: 1345135-19-4
(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

: 1345134-98-6
(2E,6R)-2,6-dimethyl-8-benzyloxy-2-octen-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.066

Reference yield:

: 1345135-19-4
(2E,6R)-ethyl 2,6-dimethyl-8-benzyloxy-2-octenoate

: 1345135-31-0
(2R,6R,10R,14E)-1,16-bis-(tert-butyldimethylsilyloxy)-12-phenylsulfonyl-2,6,10,14-tetramethyl-14-hexadecen-6-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: lithium bromide / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / Inert atmosphere

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

4.2: 0.67 h / -78 °C / Inert atmosphere

5.1: disodium hydrogenphosphate; sodium-mercury amalgam (5%) / tetrahydrofuran; methanol / 1.5 h / -15 - 20 °C

6.1: AD-mix-α; methanesulfonamide / water; tert-butyl alcohol / 0 °C

7.1: triethylamine / dichloromethane / 0 °C

8.1: potassium carbonate / methanol / 20 °C

9.1: lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

10.1: ammonia; lithium / -40 °C

11.1: pyridine / 0 °C

12.1: sodium iodide / acetone / 20 °C / Reflux

13.1: N,N-dimethyl-formamide / 6 h

14.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

14.2: -78 - 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium-mercury amalgam (5%); n-butyllithium; methanesulfonamide; AD-mix-α; ammonia; lithium; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; triethylamine; sodium iodide; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 6.1: Sharpless asymmetric dihydroxylation / 10.1: Birch reduction;
DOI:10.1016/j.tet.2011.09.066