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

Base Information

• Chemical Name: (5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal
• CAS No.: 854931-15-0
• Molecular Formula: C₃₁H₄₈O₆Si
• Molecular Weight: 544.804
• Mol file: 854931-15-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal 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%

{1-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane (854931-14-9) + carbon monoxide (201230-82-2) → (5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal (854931-15-0)

Guidance literature:

With Rh(acac)2(CO)2; triarylphosphite-based ligand; hydrogen;

DOI:10.1021/ol050511w

Reference yield:

(2R,3R)-2-((benzyloxy)methoxy)hex-5-en-3-ol → (5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal (854931-15-0)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; Rh(acac)2(CO)2; triarylphosphite-based ligand; hydrogen; potassium hydride; sodium hydrogencarbonate; ozone; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050511w

Reference yield:

1-[(R)-1-((R)-1-Benzyloxymethoxy-ethyl)-but-3-enyloxymethyl]-4-methoxy-benzene → (5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal (854931-15-0)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; Rh(acac)2(CO)2; triarylphosphite-based ligand; hydrogen; sodium hydrogencarbonate; ozone; magnesium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050511w

upstream raw materials:

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

carbon monoxide

(R)-2-((benzyloxy)methoxy)propanal

2-Methylpropyl (R)-2-(benzyloxymethoxy)propanoate

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

(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

[(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

(8S,10R,11R)-11-Benzyloxymethoxy-8-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-3,3-dimethyl-dodec-1-en-4-one