Technology Process of (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester
There total 16 articles about (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid 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:
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1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7
(5S,6R,7R,8S)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester
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79305-58-1,86334-70-5
(4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester
- Guidance literature:
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With
toluene-4-sulfonic acid;
for 3h;
Ambient temperature;
DOI:10.1139/v83-101
- Guidance literature:
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Multi-step reaction with 8 steps
1: 1.) Br2, 2.) Dowex / 1.) HOAc, 2.) MeOH
2: 1.) n-BuLi / 1.) -78 deg C
3: DMAD / acetic acid
4: 100 percent / H2, K2CO3 / 10percent Pd/C / ethyl acetate / 6 h / 2585.7 Torr
5: 90 percent / NaOMe / methanol / 2 h / 25 °C
6: 74 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / 0 °C
7: 77 percent / H2 / W-2 Raney Ni / ethanol / 4 h / 25 °C
8: 1.) p-TsOH, 2.) K2CO3 / 1.) 25 deg C, 4 h, 2.) 1 h
With
n-butyllithium; dowex; hydrogen; bromine; sodium methylate; lithium triethylborohydride; potassium carbonate; toluene-4-sulfonic acid;
palladium on activated charcoal; W-2 Raney Ni;
In
tetrahydrofuran; methanol; ethanol; acetic acid; ethyl acetate;
DOI:10.1021/jo00279a011