(4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one

Base Information

• Chemical Name: (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one
• CAS No.: 478490-98-1
• Molecular Formula: C₂₅H₃₄O₃Si
• Molecular Weight: 410.629
• Mol file: 478490-98-1.mol

Synonyms:(4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one

Chemical Property of (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one

There total 3 articles about (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one 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:

Acetyl bromide (506-96-7) + (3S,5R)-5-(tert-butyldiphenylsilyloxy)-3-methylhexanal (478490-97-0) → (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one (478490-98-1) + (S)-4-[(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-oxetan-2-one

Guidance literature:

Acetyl bromide; With N-ethyl-N,N-diisopropylamine; (R,R)-Bn-N[-CH₂-CH(iPr)N(Tf)-]2Al-Me; In dichloromethane; at -50 ℃;

(3S,5R)-5-((tert-butyldiphenylsilyl)oxy)-3-methylhexanal; In dichloromethane; at -50 ℃; for 16h; Further stages.;

DOI:10.1021/ja028019k

Reference yield:

(3R,5R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hexan-1-ol → (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one (478490-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / Heating

2.1: iPr₂NEt / (R,R)-Bn-N[-CH₂-CH(iPr)N(Tf)-]2Al-Me / CH₂Cl₂ / -50 °C

2.2: CH₂Cl₂ / 16 h / -50 °C

With N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; (R,R)-Bn-N[-CH₂-CH(iPr)N(Tf)-]2Al-Me; In dichloromethane;

DOI:10.1021/ja028019k

Reference yield:

(3S,5R)-5-(tert-butyldiphenylsilyloxy)-3-methylhexanoic acid (478490-96-9) → (4R,2'S,4'R)-4-[4'-(tert-butyldiphenylsilyloxy)-2-methylpentyl]oxetan-2-one (478490-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*SMe₂ / tetrahydrofuran; diethyl ether / 1 h / Heating

2.1: 85 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / Heating

3.1: iPr₂NEt / (R,R)-Bn-N[-CH₂-CH(iPr)N(Tf)-]2Al-Me / CH₂Cl₂ / -50 °C

3.2: CH₂Cl₂ / 16 h / -50 °C

With dimethylsulfide borane complex; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; (R,R)-Bn-N[-CH₂-CH(iPr)N(Tf)-]2Al-Me; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja028019k

upstream raw materials:

Acetyl bromide

(3S,5R)-5-(tert-butyldiphenylsilyloxy)-3-methylhexanal

(3S,5R)-5-(tert-butyldiphenylsilyloxy)-3-methylhexanoic acid

Downstream raw materials:

(2R,4S)-2-[(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-pentyl]-3,4-dihydro-2H-pyran-4-ol

(2R,2'S,4'R)-2-[4-(tert-butyldiphenylsilyloxy)-2-methylpentyl]-2,3-dihydropyran-4-one