(3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one

Base Information

• Chemical Name: (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one
• CAS No.: 195517-66-9
• Molecular Formula: C₃₂H₃₈O₃Si
• Molecular Weight: 498.737
• Mol file: 195517-66-9.mol

Synonyms:(3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one

Chemical Property of (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one

There total 13 articles about (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one 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: 41.0%

1-[(2R,3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((E)-1-methyl-buta-1,3-dienyl)-3,6-dihydro-2H-pyran-2-yl]-pent-3-yn-2-one → (3S,4aR,10aS,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one (195517-67-0) + (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one (195517-66-9)

Guidance literature:

With hydroquinone; In toluene; at 200 ℃; for 24h;

DOI:10.1021/jo970999h

Reference yield:

3-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-1-propene (129230-32-6) → (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one (195517-66-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Et₃N, 2.) imidazole / 1.) MeOH, H₂O, 2.) DMF

2: 98 percent / DMAP, DCC / CH₂Cl₂ / 5.5 h / Ambient temperature

3: 1.) HMDS, n-BuLi, TBSCl, DMPU, 3.) DMPU, KF*2H₂O, KHCO₃ / 1.) THF, hexane, -78 deg C to 0 deg C; 0 deg C, 2.5 h, 2.) toluene, reflux, 7 h, 3.) H₂O, room temperature, overnight

4: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) THF, H₂O, tert-butyl alcohol, 3 h, 2.) EtOH, H₂O, 30 min

5: 98 percent / P-TsOH / CH₂Cl₂ / 30 h / Ambient temperature

6: 15.1 g / DIBALH / diethyl ether; toluene / 0.33 h / -78 °C

7: 80 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

8: 2.) AcCl, 3.) Pd(PPh₃)4 / 1.) THF, -78 deg C, 20 min, 2.) CH₂Cl₂, pyridine, 0 deg C, 30 min, 3.) THF, 75 deg C, 24 h

9: 78 percent / CF₃COOH / tetrahydrofuran; H₂O / 20 h / Ambient temperature

10: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

11: 1.) n-BuLi, 2.) Dess-Martin periodinane / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temperature

12: 41 percent / hydroquinone / toluene / 24 h / 200 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium fluoride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N-methyl-2-indolinone; diisobutylaluminium hydride; potassium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; tert-butyldimethylsilyl chloride; triethylamine; acetyl chloride; hydroquinone; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jo970999h

Reference yield:

(2R,3R,6R)-6-allyl-2-[(tert-butyldimethylsilanyloxy)methyl]-3-hydroxy-3,6-dihydro-2H-pyran (195517-59-0) → (3S,4aR,10aR,10bR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-7,10a-dimethyl-3,4a,5,8,10a,10b-hexahydro-benzo[f]chromen-6-one (195517-66-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / DMAP, DCC / CH₂Cl₂ / 5.5 h / Ambient temperature

2: 1.) HMDS, n-BuLi, TBSCl, DMPU, 3.) DMPU, KF*2H₂O, KHCO₃ / 1.) THF, hexane, -78 deg C to 0 deg C; 0 deg C, 2.5 h, 2.) toluene, reflux, 7 h, 3.) H₂O, room temperature, overnight

3: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) THF, H₂O, tert-butyl alcohol, 3 h, 2.) EtOH, H₂O, 30 min

4: 98 percent / P-TsOH / CH₂Cl₂ / 30 h / Ambient temperature

5: 15.1 g / DIBALH / diethyl ether; toluene / 0.33 h / -78 °C

6: 80 percent / Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

7: 2.) AcCl, 3.) Pd(PPh₃)4 / 1.) THF, -78 deg C, 20 min, 2.) CH₂Cl₂, pyridine, 0 deg C, 30 min, 3.) THF, 75 deg C, 24 h

8: 78 percent / CF₃COOH / tetrahydrofuran; H₂O / 20 h / Ambient temperature

9: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

10: 1.) n-BuLi, 2.) Dess-Martin periodinane / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temperature

11: 41 percent / hydroquinone / toluene / 24 h / 200 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium fluoride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N-methyl-2-indolinone; diisobutylaluminium hydride; potassium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; tert-butyldimethylsilyl chloride; triethylamine; acetyl chloride; hydroquinone; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jo970999h

upstream raw materials:

3-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-1-propene

(2R,3R,6R)-6-allyl-2-[(tert-butyldimethylsilanyloxy)methyl]-3-hydroxy-3,6-dihydro-2H-pyran

Propionic acid (2R,3R,6R)-6-allyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester

2-[(2R,3R,6S)-2-Allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-propionic acid methyl ester