(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

Base Information

Chemical Name:(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
CAS No.:79305-58-1
Molecular Formula:C₂₆H₃₀O₉
Molecular Weight:486.519
Hs Code.:

(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property 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

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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:

Reference yield: 90.0%

: 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

: 77-76-9
2,2-dimethoxy-propane

: 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:: With toluene-4-sulfonic acid; for 3h; Ambient temperature;
DOI:10.1139/v83-101

Reference yield: 81.0%

: 1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7
(+/-)-methyl epipodophyllate

: 77-76-9
2,2-dimethoxy-propane

: 79305-58-1,86334-70-5
methyl epipodophyllate 4,11-acetonide

Guidance literature:: With toluene-4-sulfonic acid;
DOI:10.1021/ja00410a038

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 79305-58-1,86334-70-5
methyl epipodophyllate 4,11-acetonide

Guidance literature:: 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