9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

Base Information

Chemical Name:9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one
CAS No.:303998-49-4
Molecular Formula:C₄₂H₆₂O₆Si₂
Molecular Weight:719.122
Hs Code.:

9-{3-[3-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1a<i>H</i>-1-oxa-cyclopropa[<i>g</i>]chrysen-5-one

Synonyms:9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

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Chemical Property of 9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

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Technology Process of 9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

There total 19 articles about 9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-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:

: (1aS,1bR,3R,5aR,5bS,11bR,11cS)-9-[(Z)-(1S,2R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1,4,5-trimethyl-hex-4-enyl]-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

: 303998-49-4
9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

Guidance literature:: With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In decane; dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ja0024892

Reference yield:

: (2R,4bR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-11-triethylsilanyloxy-2,3,4a,4b,5,6,12,12a-octahydro-1H-chrysen-4-one

: 303998-49-4
9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

Guidance literature:: Multi-step reaction with 19 steps

1.1: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / -78 °C

2.1: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 46 h / 23 °C

3.1: 89 percent / p-TsOH / CH₂Cl₂; methanol / 0.08 h / 23 °C

4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

5.1: 856 mg / O₂; Pd(OAc)2; 2,6-di-tert-butyl-4-methylpyridine / dimethylsulfoxide / 12 h / 25 °C

6.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C

7.1: 564 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 20 h / 0 °C

8.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 25 °C

9.1: Pd(Ph₃P)4; Et₂NH / CH₂Cl₂ / 3 h / Heating

10.1: 690 mg / Et₃N / CH₂Cl₂ / 18 h / 23 °C

11.1: H₂; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr

12.1: 560 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

13.1: 91 percent / K₂CO₃ / methanol; H₂O; CH₂Cl₂ / 2.5 h / 25 °C

14.1: MgI₂; NaI / CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

15.1: CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

15.2: 72 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -66 - 25 °C

16.1: 76 percent / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 44 h / 0 °C

17.1: 74 percent / LiCl; CuCl / Pd(PPh)3 / dimethylsulfoxide / 46 h / 20 - 60 °C

18.1: H₂ / Rh(nbd)(dppb)BF₄ / CH₂Cl₂ / 45 h / 0 °C / 760.05 Torr

19.1: 18 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 2 h / 0 °C

With tert.-butylhydroperoxide; dmap; palladium diacetate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,6-di-tert-butyl-4-methylpyridine; bis(acetylacetonate)oxovanadium; hydrogen; oxygen; L-Selectride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; copper(l) chloride; lithium chloride; magnesium iodide; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; 17.1: Stille reaction;
DOI:10.1021/ja0024892

Reference yield:

: 303998-25-6
(4bR,8R,10S,10aR,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-7,8,9,10,10a,10b,11,12-octahydro-4bH-chrysen-5-one

: 303998-49-4
9-{3-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-oxiranyl]-2-hydroxy-1-methyl-propyl}-3-(dimethyl-phenyl-silanyl)-1b-hydroxy-5a-methyl-1b,2,3,4,5a,5b,6,7,11b,11c-decahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C

2.1: 564 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 20 h / 0 °C

3.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 25 °C

4.1: Pd(Ph₃P)4; Et₂NH / CH₂Cl₂ / 3 h / Heating

5.1: 690 mg / Et₃N / CH₂Cl₂ / 18 h / 23 °C

6.1: H₂; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr

7.1: 560 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

8.1: 91 percent / K₂CO₃ / methanol; H₂O; CH₂Cl₂ / 2.5 h / 25 °C

9.1: MgI₂; NaI / CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

10.1: CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

10.2: 72 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -66 - 25 °C

11.1: 76 percent / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 44 h / 0 °C

12.1: 74 percent / LiCl; CuCl / Pd(PPh)3 / dimethylsulfoxide / 46 h / 20 - 60 °C

13.1: H₂ / Rh(nbd)(dppb)BF₄ / CH₂Cl₂ / 45 h / 0 °C / 760.05 Torr

14.1: 18 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 2 h / 0 °C

With tert.-butylhydroperoxide; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(acetylacetonate)oxovanadium; hydrogen; L-Selectride; potassium carbonate; Dess-Martin periodane; acetic acid; diethylamine; triethylamine; sodium iodide; copper(l) chloride; lithium chloride; magnesium iodide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; decane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; 12.1: Stille reaction;
DOI:10.1021/ja0024892