tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane
• CAS No.: 220094-56-4
• Molecular Formula: C₃₆H₆₀O₆Si
• Molecular Weight: 616.954
• Mol file: 220094-56-4.mol

Synonyms:tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane

Chemical Property of tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane

There total 6 articles about tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane 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: 85.0%

(4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane (162189-53-9) → tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane (220094-56-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.75h;

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) → tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane (220094-56-4)

Guidance literature:

Multi-step reaction with 5 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

With methanol; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1055/s-1999-3671

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) → tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane (220094-56-4)

Guidance literature:

Multi-step reaction with 6 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

With methanol; sodium tetrahydroborate; sodium amalgam; tributylphosphine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1055/s-1999-3671

upstream raw materials:

(4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

(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

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

Downstream raw materials:

(S)-4-{(4S,5R,6S)-6-[(E)-(1S,4R,5S,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-4-methoxy-but-2-ynoic acid ethyl ester

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

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

(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