(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester
CAS No.:303958-11-4
Molecular Formula:C₂₄H₂₆O₉
Molecular Weight:458.465
Hs Code.:

(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

Synonyms:(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

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Chemical Property of (3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

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Technology Process of (3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

There total 7 articles about (3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-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: 55.0%

: 303958-10-3
(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

: 303958-11-4
(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

Guidance literature:: With perchloric acid; In diethyl ether; at 25 ℃;
DOI:10.1016/S0040-4039(00)01136-9

Reference yield:

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

: 303958-11-4
(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 25 °C

3: K₂CO₃ / acetone / 25 °C

4: 68 percent / n-BuLi / tetrahydrofuran / -40 - 25 °C

5: 55 percent / aq. HClO₄ / diethyl ether / 25 °C

With sodium hydroxide; n-butyllithium; perchloric acid; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 1: Hydrolysis / 2: Oxidation / 3: oxidative esterification / 4: Wittig methylenation / 5: Hydrolysis;
DOI:10.1016/S0040-4039(00)01136-9

Reference yield:

: 303958-08-9
8-(tert-butyl-dimethyl-silanyloxy)-7-formyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

: 303958-11-4
(3aS,4S,5R,10bS)-2-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-2,3,3a,4,5,10b-hexahydro-1,7,9-trioxa-dicyclopenta[a,g]naphthalene-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 68 percent / n-BuLi / tetrahydrofuran / -40 - 25 °C

2: 55 percent / aq. HClO₄ / diethyl ether / 25 °C

With n-butyllithium; perchloric acid; In tetrahydrofuran; diethyl ether; 1: Wittig methylenation / 2: Hydrolysis;
DOI:10.1016/S0040-4039(00)01136-9