[(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

Base Information

• Chemical Name: [(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
• CAS No.: 162189-61-9
• Molecular Formula: C₄₅H₆₄O₉Si
• Molecular Weight: 777.083
• Mol file: 162189-61-9.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 14 articles about [(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 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: 98.0%

[(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) → [(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 (162189-61-9)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

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)-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 (162189-61-9)

Guidance literature:

Multi-step reaction with 13 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

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; 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) → [(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 (162189-61-9)

Guidance literature:

Multi-step reaction with 12 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

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; 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:

[(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

(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:

(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

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