(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

Base Information

Chemical Name:(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol
CAS No.:210687-18-6
Molecular Formula:C₄₁H₅₈O₃
Molecular Weight:598.91
Hs Code.:

(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

Synonyms:(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

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Chemical Property of (2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

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Technology Process of (2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

There total 12 articles about (2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol 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: 54.0%

: 210687-17-5
[(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptyloxy]-tert-butyl-dimethyl-silane

: 210687-18-6
(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 16h;
DOI:10.1021/jo980266c

Reference yield:

: 100-39-0
benzyl bromide

: 210687-18-6
(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 16 h / Heating

2: 52 percent / zinc amalgam, hydrochloric acid / ethanol / 1.6 h / Heating

3: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h

4: 0.59 g / PDC / CH₂Cl₂ / 2 h

5: 94 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

6: 50 percent / Bu₃SnH, Pd(PPh₃)4, LiCl / tetrahydrofuran / 16 h / Heating

7: 54 percent / Bu₄NF / tetrahydrofuran / 16 h

With hydrogenchloride; amalgamated zinc; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo980266c

Reference yield:

: 146333-24-6
3-O-benzyl diosgenin

: 210687-18-6
(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) BH₃-SMe₂, 2.) H₂O₂, NaOH / 1.) THF, 0 deg C, 0.1 h, room temperature, 20 h, 2.) ethanol, water, reflux, 1 h

2: 95 percent / PDC / CH₂Cl₂ / 2 h

3: 100 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.2 h

4: 75 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 16 h / Heating

5: 52 percent / zinc amalgam, hydrochloric acid / ethanol / 1.6 h / Heating

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h

7: 0.59 g / PDC / CH₂Cl₂ / 2 h

8: 94 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

9: 50 percent / Bu₃SnH, Pd(PPh₃)4, LiCl / tetrahydrofuran / 16 h / Heating

10: 54 percent / Bu₄NF / tetrahydrofuran / 16 h

With hydrogenchloride; sodium hydroxide; amalgamated zinc; lithium aluminium tetrahydride; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/jo980266c