Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester
CAS No.:113626-96-3
Molecular Formula:C₂₇H₃₄O₄S
Molecular Weight:454.631
Hs Code.:

Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

There total 7 articles about Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl 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:

: 30905-78-3
methyl 12-methoxy-8,11,13-abietatrien-18-oate

: 113626-96-3
Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 15.9 percent / AlCl₃ / CH₂Cl₂ / 6 deg C to 9 deg C, 13 min, RT, 40 min

2: potassium carbonate / butan-2-one / 8 h / Heating

3: 10 percent aq. sodium hydroxide / ethanol / 1 h / Heating

4: sodium acetate / acetic anhydride / 7.5 h / Heating

5: H₂ / 10 percent Pd-C / acetic acid; aq. HClO₄ / Ambient temperature

6: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

7: pyridine / 5.5 h / 95 - 100 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; hydrogen; sodium acetate; potassium carbonate; palladium on activated charcoal; In perchloric acid; diethyl ether; ethanol; dichloromethane; acetic anhydride; acetic acid; butanone;
DOI:10.1246/bcsj.60.2401

Reference yield:

: 113579-59-2
methyl 13-acetyl-12-hydroxy-8,11,13-abietatrien-18-oate

: 113626-96-3
Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: potassium carbonate / butan-2-one / 8 h / Heating

2: 10 percent aq. sodium hydroxide / ethanol / 1 h / Heating

3: sodium acetate / acetic anhydride / 7.5 h / Heating

4: H₂ / 10 percent Pd-C / acetic acid; aq. HClO₄ / Ambient temperature

5: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

6: pyridine / 5.5 h / 95 - 100 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium acetate; potassium carbonate; palladium on activated charcoal; In perchloric acid; diethyl ether; ethanol; acetic anhydride; acetic acid; butanone;
DOI:10.1246/bcsj.60.2401

Reference yield:

: 113579-62-7
(1R,4aS,10aR)-7-Acetyl-6-ethoxycarbonylmethoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester

: 113626-96-3
Toluene-4-sulfonic acid (4R,4aR,8S,11bS)-4,8,11b-trimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydro-10-oxa-cyclopenta[b]phenanthren-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 10 percent aq. sodium hydroxide / ethanol / 1 h / Heating

2: sodium acetate / acetic anhydride / 7.5 h / Heating

3: H₂ / 10 percent Pd-C / acetic acid; aq. HClO₄ / Ambient temperature

4: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

5: pyridine / 5.5 h / 95 - 100 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium acetate; palladium on activated charcoal; In perchloric acid; diethyl ether; ethanol; acetic anhydride; acetic acid;
DOI:10.1246/bcsj.60.2401