(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

Base Information

Chemical Name:(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester
CAS No.:853023-12-8
Molecular Formula:C₂₈H₄₆O₅Si
Molecular Weight:490.756
Hs Code.:

Synonyms:(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

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Chemical Property of (R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

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Technology Process of (R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

There total 6 articles about (R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-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: 81.0%

: 415900-37-7
(Z)-(10S)-11-(tert-butyldimethylsilyloxy)-3-hydroxy-6,10-dimethyl-5-undecen-2-one

: 3966-32-3
(R)-methoxyphenylacetic acid

: 853023-12-8
(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo401355r

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 853023-12-8
(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2: water; potassium carbonate / methanol / 0.23 h / 20 °C

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; water; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo401355r

Reference yield:

: 796965-84-9
(4Z,8E)-2-acetoxy-2-acetyl-5,9-dimethyl-10-hydroxy-deca-4,8-dienoic-acid-tert-butylester

: 853023-12-8
(R)-α-methoxyphenylacetic acid (Z)-(1S,8S)-1-acetyl-9-(tertbutyldimethylsilyloxy)-4,8-dimethylnon-3-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; hydrogen / water; methanol / 22 h / 20 °C / 75007.5 Torr / Autoclave

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

3: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

4: water; potassium carbonate / methanol / 0.23 h / 20 °C

5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

With dmap; Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; water; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; water;
DOI:10.1021/jo401355r