(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

Base Information

• Chemical Name: (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
• CAS No.: 220094-57-5
• Molecular Formula: C₃₉H₆₄O₈Si
• Molecular Weight: 689.018
• Mol file: 220094-57-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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%

chloroformic acid ethyl ester (541-41-3) + 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) → (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 (220094-57-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -50 - 40 ℃; for 1h;

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) → (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 (220094-57-5)

Guidance literature:

Multi-step reaction with 6 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

With methanol; sodium amalgam; n-butyllithium; 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) → (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 (220094-57-5)

Guidance literature:

Multi-step reaction with 7 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

With methanol; sodium tetrahydroborate; sodium amalgam; n-butyllithium; 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:

chloroformic acid ethyl ester

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

(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:

[(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

[(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