[(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

Base Information

• Chemical Name: [(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
• CAS No.: 220094-58-6
• Molecular Formula: C₅₂H₇₈O₁₀Si₂
• Molecular Weight: 919.356
• Mol file: 220094-58-6.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 13 articles about [(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 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: 90.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + [(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 methyl 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 (220094-58-6)

Guidance literature:

With titanium(IV) isopropylate; at 100 ℃; for 96h;

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) → [(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 (220094-58-6)

Guidance literature:

Multi-step reaction with 13 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

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; 3-chloro-benzenecarboperoxoic acid; 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) → [(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 (220094-58-6)

Guidance literature:

Multi-step reaction with 12 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

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; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1999-3671

upstream raw materials:

2-(Trimethylsilyl)ethanol

(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:

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

(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

[(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