Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Base Information

Chemical Name:Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester
CAS No.:64492-99-5
Molecular Formula:C₃₃H₄₈O₅S
Molecular Weight:556.807
Hs Code.:

Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

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Chemical Property of Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

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Technology Process of Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

There total 2 articles about Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl 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:

: 31300-52-4
3β-acetoxy-9,19-cyclo-4,4,14α-trimethyl-5α-pregnan-20-one

: 64492-99-5
Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH₄ / aq. ethanol; CHCl₃ / 7 h / 0 °C

2: pyridine / 1) 0 grad C, 10 min; 2) 10-15 grad C, 30 hr

With sodium tetrahydroborate; In pyridine; ethanol; chloroform;
DOI:10.1016/S0040-4020(01)92368-3

Reference yield:

: 38037-06-8
(20R)-3β-acetoxy-9,19-cyclo-4,4,14α-trimethyl-5α-pregnan-20-ol

: 98-59-9
p-toluenesulfonyl chloride

: 64492-99-5
Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Guidance literature:: In pyridine; Yield given; 1) 0 grad C, 10 min; 2) 10-15 grad C, 30 hr;
DOI:10.1016/S0040-4020(01)92368-3

Reference yield:

: 64492-99-5
Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

: 1053-21-0
cyclobuxophyllinine-M

Guidance literature:: Multi-step reaction with 9 steps

1: sym-collidine / 3 h / Heating

2: 1) O₂ / 1) methylene blue, sunlight / 1)pyridine, 35 hr; 2) Ac₂O, 30 grad C, 45 min, 60 grad C, 1 hr

3: 86.7 percent / LAH / diethyl ether / 6 h / 0 °C

4: 80 percent / p-toluenesulphonic acid / 0.33 h / 12 °C

5: 80 percent / pyridinium chromate-on-silica gel / CH₂Cl₂; acetic acid / 6 h / Ambient temperature

6: 88.4 percent / p-toluenesulphonic acid / acetic acid; acetic anhydride / 48 h / Ambient temperature

7: 67 percent / NaBH₃CN, 4A molecular sieves / methanol / 80 h / Ambient temperature

8: 1) KOH; 2) MnO₂ / 1) MeOH, reflux, 4 hr; 2) C₆H₆, rt, 12 hr

9: KOH / aq. ethanol / 2 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; manganese(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; pyridinium chromate-on-silica gel; 4 A molecular sieve; oxygen; sodium cyanoborohydride; methylene blue; toluene-4-sulfonic acid; In methanol; diethyl ether; ethanol; dichloromethane; acetic anhydride; acetic acid;
DOI:10.1016/S0040-4020(01)92368-3