Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester

Base Information

• Chemical Name: Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester
• CAS No.: 220094-59-7
• Molecular Formula: C₅₃H₈₂O₉Si₂
• Molecular Weight: 919.4
• Mol file: 220094-59-7.mol

Synonyms:

Chemical Property of Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester

There total 15 articles about Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester 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:

(R)-2-{(4R,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde (162189-50-6) → Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester (220094-59-7)

Guidance literature:

Multi-step reaction with 15 steps

1: NaBH₄ / ethanol / 0.75 h / 0 °C

2: Bu₃P / CH₂Cl₂ / 3.5 h / 0 °C

3: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) r.t., 45 min

5: 5percent Na/Hg, MeOH / ethyl acetate / 5 h / -20 °C

6: 85 percent / TBAF / tetrahydrofuran / 0.75 h / 0 °C

7: 85 percent / BuLi / tetrahydrofuran / 1 h / -50 - 40 °C

8: 1.) morpholine, 2.) HCl, H₂O / 1.) THF, reflux, 2 h

9: 75 percent / HOAc / 2 h / 50 °C

10: 96 percent / imidazole / dimethylformamide / 168 h / -60 °C

11: 98 percent / pyridine, DMAP / 0.25 h / Ambient temperature

12: 99 percent / CSA / methanol; CH₂Cl₂ / 96 h / Ambient temperature

13: 90 percent / Ti(i-OPr)4 / 96 h / 100 °C

14: 98 percent / CSF / dimethylformamide / 24 h / Ambient temperature

15: Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

With morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium amalgam; n-butyllithium; tributylphosphine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3671

Reference yield:

(S)-2-{(4S,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol (220094-53-1) → Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester (220094-59-7)

Guidance literature:

Multi-step reaction with 14 steps

1: Bu₃P / CH₂Cl₂ / 3.5 h / 0 °C

2: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) r.t., 45 min

4: 5percent Na/Hg, MeOH / ethyl acetate / 5 h / -20 °C

5: 85 percent / TBAF / tetrahydrofuran / 0.75 h / 0 °C

6: 85 percent / BuLi / tetrahydrofuran / 1 h / -50 - 40 °C

7: 1.) morpholine, 2.) HCl, H₂O / 1.) THF, reflux, 2 h

8: 75 percent / HOAc / 2 h / 50 °C

9: 96 percent / imidazole / dimethylformamide / 168 h / -60 °C

10: 98 percent / pyridine, DMAP / 0.25 h / Ambient temperature

11: 99 percent / CSA / methanol; CH₂Cl₂ / 96 h / Ambient temperature

12: 90 percent / Ti(i-OPr)4 / 96 h / 100 °C

13: 98 percent / CSF / dimethylformamide / 24 h / Ambient temperature

14: Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

With morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; dmap; sodium amalgam; n-butyllithium; tributylphosphine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3671

Reference yield:

tert-Butyl-{(S)-3-methoxy-3-[(4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-prop-1-ynyl}-dimethyl-silane (162189-51-7) → Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester (220094-59-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) r.t., 45 min

3: 5percent Na/Hg, MeOH / ethyl acetate / 5 h / -20 °C

4: 85 percent / TBAF / tetrahydrofuran / 0.75 h / 0 °C

5: 85 percent / BuLi / tetrahydrofuran / 1 h / -50 - 40 °C

6: 1.) morpholine, 2.) HCl, H₂O / 1.) THF, reflux, 2 h

7: 75 percent / HOAc / 2 h / 50 °C

8: 96 percent / imidazole / dimethylformamide / 168 h / -60 °C

9: 98 percent / pyridine, DMAP / 0.25 h / Ambient temperature

10: 99 percent / CSA / methanol; CH₂Cl₂ / 96 h / Ambient temperature

11: 90 percent / Ti(i-OPr)4 / 96 h / 100 °C

12: 98 percent / CSF / dimethylformamide / 24 h / Ambient temperature

13: Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

With morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; dmap; sodium amalgam; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3671

upstream raw materials:

chlorodimethyl(1,1,2-trimethylpropyl)silane

[(2R,3R,4S,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(1S,4R,5S,10S)-10-hydroxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-2,3-dimethoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid

(S)-2-{(4S,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol

(R)-2-{(4R,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

Downstream raw materials:

(E)-(1R,5S,10S,11R,14S,15S,16S,17S,18R)-1,17-Dihydroxy-10,11,18-trimethoxy-14,16-dimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

(E)-(1R,5S,10S,11R,14S,15S,16R,17S,18R)-17-(tert-Butyl-diphenyl-silanyloxy)-1,10,11,18-tetramethoxy-14,16-dimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one