(1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate

Base Information

• Chemical Name: (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate
• CAS No.: 894351-71-4
• Molecular Formula: C₂₉H₄₀O₃Si
• Molecular Weight: 464.72
• Mol file: 894351-71-4.mol

Synonyms:(1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate

Chemical Property of (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate

There total 4 articles about (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate 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: 77.0%

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) + acetic acid (64-19-7,77671-22-8) + C22H31ClMgOSi → (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate (894351-71-4)

Guidance literature:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate; With tert-butylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

C₂₂H₃₁ClMgOSi; In tetrahydrofuran; at -18 ℃; for 4h;

acetic acid; With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at -78 ℃; for 5h;

DOI:10.1016/j.tet.2006.03.001

Reference yield:

acetic acid (64-19-7,77671-22-8) + (1S,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopenten-1-ol (827325-78-0) → (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate (894351-71-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at -78 ℃;

DOI:10.1055/s-2004-834794

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → (1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopentenyl acetate (894351-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-BuMgCl / 0 °C

1.2: 81 percent / CuCN / 4 h / -18 °C

2.1: DIAD; PPh₃ / toluene / -78 °C

With di-isopropyl azodicarboxylate; tert-butylmagnesium chloride; triphenylphosphine; In toluene; 2.1: Mitsunobu inversion;

DOI:10.1055/s-2004-834794

upstream raw materials:

acetic acid

(1S,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopenten-1-ol

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

Downstream raw materials:

(1R,4S)-4-[6-{(tert-butyldiphenylsilyl)oxy}hexyl]-2-cyclopenten-1-ol

{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetic acid methyl ester

C₃₈H₆₂O₂Si₂

{(1S,2S,5R)-2-[6-(tert-Butyl-diphenyl-silanyloxy)-hexyl]-5-triethylsilanyloxy-cyclopentyl}-acetaldehyde