3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

Base Information

Chemical Name:3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester
CAS No.:1228023-20-8
Molecular Formula:C₃₇H₄₄BrNO₄Si
Molecular Weight:674.75
Hs Code.:

Synonyms:3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

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Chemical Property of 3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

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Technology Process of 3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

There total 10 articles about 3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl 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: 94.0%

: 67-56-1
methanol

: 1228023-15-1
O-(tert-butyldiphenylsilyl)-2-methylene-4-(2,2-dimethyl-4H-1,3-dioxin-4-one-6-yl)-5-(4-bromo-1-methylindol-3-yl)-5-methyl-hexan-1-ol

: 1228023-20-8
3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

Guidance literature:: In toluene; at 110 ℃; for 21h;
DOI:10.1021/ol1006373

Reference yield:

: 949035-05-6
4-bromo-3-acetyl-1-methyl-1H-indole

: 1228023-20-8
3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / toluene / 0.03 h / -78 °C

2.2: 19.5 h / -78 - 20 °C

3.1: toluene / 21 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.03.010

Reference yield:

: 1228023-14-0
6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

: 1228023-20-8
3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

1.2: 0.83 h / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / toluene / 0.03 h / -78 °C

2.2: 19.5 h / -78 - 20 °C

3.1: toluene / 21 h / 100 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.03.010