(S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

Base Information

• Chemical Name: (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone
• CAS No.: 115435-03-5
• Molecular Formula: C₂₉H₃₂O₃Si
• Molecular Weight: 456.657
• Mol file: 115435-03-5.mol

Synonyms:(S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

Chemical Property of (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

There total 10 articles about (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone 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:

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene (115435-01-3) → (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone (115435-03-5)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.60.3673

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone (115435-03-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 80percent acetic acid / H₂O / Heating

2: 1.) conc. HCl / 1.) -15 min, 30 min; 2.) pyridine, r.t., 13 h

3: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

4: pyridine; acetic anhydride / 36 h / Ambient temperature

5: sodium borohydride / methanol / 0.5 h / -15 °C

7: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

8: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

9: 73 percent / imidazole / dimethylformamide / Ambient temperature

10: 223 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 4 A molecular sieve; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; calcium carbonate; sodium chloride; mercury dichloride; In pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1246/bcsj.60.3673

Reference yield:

3-O-Benzyl-D-xylose → (S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone (115435-03-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) conc. HCl / 1.) -15 min, 30 min; 2.) pyridine, r.t., 13 h

2: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

3: pyridine; acetic anhydride / 36 h / Ambient temperature

4: sodium borohydride / methanol / 0.5 h / -15 °C

6: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

7: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

8: 73 percent / imidazole / dimethylformamide / Ambient temperature

9: 223 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 4 A molecular sieve; diisobutylaluminium hydride; pyridinium chlorochromate; calcium carbonate; sodium chloride; mercury dichloride; In pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1246/bcsj.60.3673

upstream raw materials:

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

(3S,4S)-4-Acetoxy-3-benzyloxy-cyclopent-1-enecarboxylic acid methyl ester

Acetic acid (1R,2S,3R)-3-acetoxy-1-acetoxymethyl-2-benzyloxy-4-oxo-butyl ester

Downstream raw materials:

(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

(3S,4R)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene

(3S,4R)-3-benzyloxy-4-hydroxy-1-cyclopentene-1-methanol