9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

Base Information

Chemical Name:9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione
CAS No.:245657-67-4
Molecular Formula:C₃₃H₃₆O₆Si
Molecular Weight:556.731
Hs Code.:

9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

Synonyms:9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

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Chemical Property of 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

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Technology Process of 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

There total 18 articles about 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione 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: 58.0%

: 176040-47-4
6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-5-hydroxy-[1,4]naphthoquinone

: 245657-04-9
Dimethyl-[1-methyl-3-((E)-2-phenylsulfanyl-vinyl)-cyclohex-3-enyl]-phenyl-silane

: 245657-67-4
9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

Guidance literature:: 6-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-5-hydroxy-[1,4]naphthoquinone; Dimethyl-[1-methyl-3-((E)-2-phenylsulfanyl-vinyl)-cyclohex-3-enyl]-phenyl-silane; With triacetoxyborane; In dichloromethane; at 25 ℃; for 1.5h;

With 1,8-diazabicyclo[5.4.0]undec-8-ene; In dichloromethane; at 25 ℃; for 0.5h;
DOI:10.1021/jo990648y

Reference yield:

: 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-6-phenylsulfanyl-1,2,3,4,6,6a,12a,12b-octahydro-benzo[a]anthracene-7,12-dione

: 245657-67-4
9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 0.5h; Yield given;
DOI:10.1039/CC9960000225

Reference yield:

: 1193-18-6
3-methylcyclohexen-2-one

: 245657-67-4
9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(dimethyl-phenyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione

Guidance literature:: Multi-step reaction with 8 steps

2: 94 percent / LDA / tetrahydrofuran / 1 h / -78 - 25 °C

3: 93 percent / LiCl / (Ph₃P)4Pd / dimethylformamide / 1 h / 70 °C

4: H2O, AD-mix-β / 2-methyl-propan-2-ol / 12 h / 0 °C

5: aq. NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 1.5 h / 25 °C

6: 77 percent / tetrahydrofuran / 0.5 h / 25 °C

7: B(OAc)3 / CH₂Cl₂ / 2 h / 25 °C

8: DBU / CH₂Cl₂ / 0.5 h / 25 °C

With sodium periodate; triacetoxyborane; AD-mix-β; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/CC9960000225