(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

Base Information

• Chemical Name: (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
• CAS No.: 172099-36-4
• Molecular Formula: C₃₉H₅₄O₄Si
• Molecular Weight: 614.941
• Mol file: 172099-36-4.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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:

3β-acetoxy-5α-pregn-16-ene-12,20-dione (2611-38-3) → (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 (172099-36-4)

Guidance literature:

Multi-step reaction with 12 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

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; 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:

hecogenin acetate → (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 (172099-36-4)

Guidance literature:

Multi-step reaction with 13 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

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; 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:

(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-carboxylic acid ethyl ester → (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 (172099-36-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 0.166667h;

DOI:10.1016/0040-4039(95)01804-Q

upstream raw materials:

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

(20R)-12-Oxo-5α-pregnan-3β,20-diol-3-acetat

tert-butylchlorodiphenylsilane

(3R,3aS,5aS,5bR,7aS,9S,11aS,11bS,13aR)-9-Hydroxy-3,11a-dimethyl-hexadecahydro-2-oxa-pentaleno[1,6a-a]phenanthrene-1,13-dione

Downstream raw materials:

(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