(3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene

Base Information

• Chemical Name: (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene
• CAS No.: 865302-28-9
• Molecular Formula: C₂₆H₃₄O₃Si
• Molecular Weight: 422.64
• Mol file: 865302-28-9.mol

Synonyms:(3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene

Chemical Property of (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene

There total 4 articles about (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene 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: 96.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (1S,4R)-4-hydroxycyclopent-2-enyl 2,2,2-trimethylacetate (178034-12-3) → (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene (865302-28-9)

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran; at 22 ℃; for 2h;

DOI:10.1021/ol051415y

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene (865302-28-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 0 °C

2: 95 percent / K₂CO₃ / methanol / 0.33 h / 22 °C

3: 96 percent / silver(I) nitrate; pyridine / tetrahydrofuran / 2 h / 22 °C

With pyridine; dmap; potassium carbonate; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol051415y

Reference yield:

pivaloyl chloride (3282-30-2) → (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene (865302-28-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 0 °C

2: 95 percent / K₂CO₃ / methanol / 0.33 h / 22 °C

3: 96 percent / silver(I) nitrate; pyridine / tetrahydrofuran / 2 h / 22 °C

With pyridine; dmap; potassium carbonate; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol051415y

upstream raw materials:

tert-butylchlorodiphenylsilane

(1S,4R)-4-hydroxycyclopent-2-enyl 2,2,2-trimethylacetate

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

pivaloyl chloride

Downstream raw materials:

(4R)-(+)-2-bromo-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one

(4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one

C₆₀H₉₆NO₁₁PSi

(4R,5R)-(+)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(2Z-octenyl)-α-[(1R,2R)-1,2-epoxy-6-(4-methoxyphenylmethoxy)hexyl]cyclopent-2-enemethanol