(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

Base Information

• Chemical Name: (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal
• CAS No.: 198541-55-8
• Molecular Formula: C₂₆H₃₂O₄Si
• Molecular Weight: 436.623
• Mol file: 198541-55-8.mol

Synonyms:(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

Chemical Property of (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

There total 10 articles about (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal 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:

3-[2-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-pentyl]-5-methyl-5H-furan-2-one → (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal (198541-55-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2h;

DOI:10.1002/anie.200290038

Reference yield:

(R)-7-(4-Methoxybenzyloxy)hept-1-en-4-ol (500594-11-6) → (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal (198541-55-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: imidazole / dimethylformamide / 6 h / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 24 h / 0 - 20 °C

2.2: aq. H₂O₂; NaOH / tetrahydrofuran / 0 - 20 °C

3.1: Jones reagent / acetone / 0.5 h / 0 °C

4.1: diethyl ether / 0.5 h / 0 °C

5.1: LDA / tetrahydrofuran / 1 h / -78 °C

6.1: 10-camphorsulfonic acid; H₂O / methanol / 4 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 1.5 h / -10 °C

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h / -10 °C

9.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / aq. phosphate buffer; CH₂Cl₂ / 0 - 2 °C / pH 7.4

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

With 1H-imidazole; jones reagent; borane-THF; oxalyl dichloride; (1S)-10-camphorsulfonic acid; water; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 3.1: Jones oxidation / 10.1: Swern oxidation;

DOI:10.1002/anie.200290038

Reference yield:

(R)-tert.-Butyl(7-(4-methoxybenzyloxy)hept-1-en-4-yloxy)diphenylsilane → (R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal (198541-55-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BH₃*THF / tetrahydrofuran / 24 h / 0 - 20 °C

1.2: aq. H₂O₂; NaOH / tetrahydrofuran / 0 - 20 °C

2.1: Jones reagent / acetone / 0.5 h / 0 °C

3.1: diethyl ether / 0.5 h / 0 °C

4.1: LDA / tetrahydrofuran / 1 h / -78 °C

5.1: 10-camphorsulfonic acid; H₂O / methanol / 4 h / 20 °C

6.1: Et₃N / CH₂Cl₂ / 1.5 h / -10 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h / -10 °C

8.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / aq. phosphate buffer; CH₂Cl₂ / 0 - 2 °C / pH 7.4

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

With jones reagent; borane-THF; oxalyl dichloride; (1S)-10-camphorsulfonic acid; water; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; acetone; 2.1: Jones oxidation / 9.1: Swern oxidation;

DOI:10.1002/anie.200290038

upstream raw materials:

(R)-7-(4-Methoxybenzyloxy)hept-1-en-4-ol

4-(tert-butyl-diphenyl-silanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid methyl ester

3-[2-(tert-butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-pentyl]-5-methyl-5H-furan-2-one

Downstream raw materials:

(S)-3-[(Z)-(2R,8S,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-((2R,5R,6R)-6-dodecyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-8,13-bis-methoxymethoxy-tridec-5-enyl]-5-methyl-5H-furan-2-one

(S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one

(S)-3-((R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2R,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-nonyl)-5-methyl-5H-furan-2-one

(S)-3-((E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-9-{(2S,5S)-5-[(1S,4S)-4-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-1,4-bis-methoxymethoxy-butyl]-tetrahydro-furan-2-yl}-non-5-en-7-ynyl)-5-methyl-5H-furan-2-one