(4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 875303-42-7
• Molecular Formula: C₃₄H₅₂O₆Si₂
• Molecular Weight: 612.954
• Mol file: 875303-42-7.mol

Synonyms:(4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane

There total 8 articles about (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane 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: 99.0%

(4S,5R)-5-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (875303-41-6) + (methoxymethylene)triphenylphosphorane (20763-19-3) → (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane (875303-42-7)

Guidance literature:

DOI:10.1055/s-2005-918960

Reference yield:

(E)-(S)-4-Hydroxy-4-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid tert-butyl ester (875303-35-8) → (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane (875303-42-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / Et₃N; DMAP

2: 100 percent / imidazole; DMAP / dimethylformamide / 50 °C

3: 95 percent / DIBAL-H; NaBH₄ / CH₂Cl₂; tetrahydrofuran; methanol

4: 99 percent / i-Pr₂NEt; Bu₄NI

5: 93 percent / NBS / dimethylsulfoxide; H₂O / 20 °C

6: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-2005-918960

Reference yield:

(E)-(S)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-hydroxy-but-2-enoic acid tert-butyl ester (875303-36-9) → (4R,5R)-4-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-5-((Z)-2-methoxy-vinyl)-2,2-dimethyl-[1,3]dioxolane (875303-42-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / imidazole; DMAP / dimethylformamide / 50 °C

2: 95 percent / DIBAL-H; NaBH₄ / CH₂Cl₂; tetrahydrofuran; methanol

3: 99 percent / i-Pr₂NEt; Bu₄NI

4: 93 percent / NBS / dimethylsulfoxide; H₂O / 20 °C

5: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-2005-918960

upstream raw materials:

(4S,5R)-5-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

(methoxymethylene)triphenylphosphorane

(E)-(S)-4-Hydroxy-4-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid tert-butyl ester

(E)-(S)-4-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-hydroxy-but-2-enoic acid tert-butyl ester

Downstream raw materials:

{(4R,5R)-5-[(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-(2-trimethylsilanyl-ethoxymethoxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetaldehyde

{(4R,5S)-5-[(3aR,4R,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

(R)-1-{(3aR,4S,6R,7aR)-2,2-Dimethyl-4-[(E)-3-(2-trimethylsilanyl-ethoxymethoxy)-propenyl]-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl}-2-trityloxy-ethanol

(2-{(E)-3-[(3aR,4S,6R,7aR)-6-((R)-1-Methoxymethoxy-2-trityloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-allyloxymethoxy}-ethyl)-trimethyl-silane