(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

Base Information

Chemical Name:(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde
CAS No.:171525-83-0
Molecular Formula:C₃₉H₅₀O₄Si
Molecular Weight:610.909
Hs Code.:

(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

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Chemical Property of (4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

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Technology Process of (4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

There total 16 articles about (4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde 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:

: hecogenin acetate

: 171525-83-0
(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1: 60 percent / modified Dauben procedure

2: 1.) PPTS; 2.) MgSO₄, H₂O / 1.) benzene, 80 deg C, 4.5 h; 2.) benzene, r.t., overnight

3: 86 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 0.17 h / 25 °C

4: 99 percent / H₂ / PtO₂ / CH₂Cl₂ / 0.75 h / 25 °C

5: 78 percent / PPTs / acetone; H₂O / 6 h / 80 °C

6: 1.) Pb(OAc)4, I₂; 2.) H₂CrO₄ / 1.) cyclohexane, 80 deg C, 2 h; 2.) acetone, 0 deg C, 1 h

7: 94 percent / KHCO₃ / methanol; H₂O / 4 h / 80 - 90 °C

8: AgNO₃ / dimethylformamide / 0.17 h / 25 °C

9: LiAlH₄ / diethyl ether / 0.25 h / 40 °C

10: 96 percent / Rh₂(OAc)4 / benzene / 2.5 h / 80 °C

11: H₂CrO₄ / diethyl ether / 1.5 h / 25 °C

12: NaH / tetrahydrofuran / 1.5 h / 25 °C

13: LiAlH₄ / diethyl ether / 0.17 h / 25 °C

14: (CF₃CO)2O, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

With lead(IV) acetate; dirhodium tetraacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; water; hydrogen; iodine; pyridinium p-toluenesulfonate; chromic acid; sodium hydride; magnesium sulfate; potassium hydrogencarbonate; silver nitrate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0040-4039(95)01804-Q

Reference yield:

: 2611-38-3
3β-acetoxy-5α-pregn-16-ene-12,20-dione

: 171525-83-0
(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) PPTS; 2.) MgSO₄, H₂O / 1.) benzene, 80 deg C, 4.5 h; 2.) benzene, r.t., overnight

2: 86 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 0.17 h / 25 °C

3: 99 percent / H₂ / PtO₂ / CH₂Cl₂ / 0.75 h / 25 °C

4: 78 percent / PPTs / acetone; H₂O / 6 h / 80 °C

5: 1.) Pb(OAc)4, I₂; 2.) H₂CrO₄ / 1.) cyclohexane, 80 deg C, 2 h; 2.) acetone, 0 deg C, 1 h

6: 94 percent / KHCO₃ / methanol; H₂O / 4 h / 80 - 90 °C

7: AgNO₃ / dimethylformamide / 0.17 h / 25 °C

8: LiAlH₄ / diethyl ether / 0.25 h / 40 °C

9: 96 percent / Rh₂(OAc)4 / benzene / 2.5 h / 80 °C

10: H₂CrO₄ / diethyl ether / 1.5 h / 25 °C

11: NaH / tetrahydrofuran / 1.5 h / 25 °C

12: LiAlH₄ / diethyl ether / 0.17 h / 25 °C

13: (CF₃CO)2O, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

With lead(IV) acetate; dirhodium tetraacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; water; hydrogen; iodine; pyridinium p-toluenesulfonate; chromic acid; sodium hydride; magnesium sulfate; potassium hydrogencarbonate; silver nitrate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0040-4039(95)01804-Q

Reference yield:

: 172099-36-4
(4aS,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxymethyl-4,12a-dimethyl-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthren-14-ol

: 171525-83-0
(4aR,6aS,6bR,8aS,10S,12aS,12bS,14aS)-10-(tert-Butyl-diphenyl-silanyloxy)-4,12a-dimethyl-14-oxo-4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14-hexadecahydro-2-oxa-indeno[1,7a-a]phenanthrene-3-carbaldehyde

Guidance literature:: With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 1h; Yield given;
DOI:10.1016/0040-4039(95)01804-Q