(E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester

Base Information

• Chemical Name: (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester
• CAS No.: 854931-24-1
• Molecular Formula: C₃₉H₆₀O₇SSi
• Molecular Weight: 701.053
• Mol file: 854931-24-1.mol

Synonyms:(E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester

Chemical Property of (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester

There total 12 articles about (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-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: 92.0%

(7S,9R,10R)-10-Benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-2,2-dimethyl-3-oxo-undecanal (854931-25-2) + S-ethyl 2-(diethoxyphosphoryl) ethanethioate (3699-87-4) → (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester (854931-24-1)

Guidance literature:

With sodium hydride;

DOI:10.1021/ol050511w

Reference yield:

(2R,3R)-2-((benzyloxy)methoxy)hex-5-en-3-ol → (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester (854931-24-1)

Guidance literature:

Multi-step reaction with 9 steps

1: KH / tetrahydrofuran

2: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

3: MgBr₂*Et₂O

4: 97 percent / imidazole / dimethylformamide

5: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

6: 92 percent / indium / dimethylformamide

7: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

8: O₃

9: 92 percent / NaH

With 1H-imidazole; indium; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; hydrogen; sodium acetate; potassium hydride; sodium hydride; sodium hydrogencarbonate; ozone; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 9: Horner-Emmons reaction;

DOI:10.1021/ol050511w

Reference yield:

1-[(R)-1-((R)-1-Benzyloxymethoxy-ethyl)-but-3-enyloxymethyl]-4-methoxy-benzene → (E)-(9S,11R,12R)-12-Benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,4-dimethyl-5-oxo-tridec-2-enethioic acid S-ethyl ester (854931-24-1)

Guidance literature:

Multi-step reaction with 8 steps

1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2: MgBr₂*Et₂O

3: 97 percent / imidazole / dimethylformamide

4: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

5: 92 percent / indium / dimethylformamide

6: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

7: O₃

8: 92 percent / NaH

With 1H-imidazole; indium; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; hydrogen; sodium acetate; sodium hydride; sodium hydrogencarbonate; ozone; pyridinium chlorochromate; magnesium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide; 8: Horner-Emmons reaction;

DOI:10.1021/ol050511w

upstream raw materials:

(7S,9R,10R)-10-Benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-2,2-dimethyl-3-oxo-undecanal

S-ethyl 2-(diethoxyphosphoryl) ethanethioate

{1-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane

(5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal

Downstream raw materials:

{2-[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-acetaldehyde

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enethioic acid S-ethyl ester

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal