(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol

Base Information

• Chemical Name: (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol
• CAS No.: 126798-07-0
• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.43
• Mol file: 126798-07-0.mol

Synonyms:(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol

Chemical Property of (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol

There total 6 articles about (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol 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: 39.0%

acetic anhydride (108-24-7) + (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-2-cyclopentene-4,5-diol (126798-05-8) → (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol (126798-07-0) + (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-5-(acetyloxy)-2-cyclopenten-4-ol (126798-08-1) + (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-bis(acetyloxy)-2-cyclopentene (126798-06-9)

Guidance literature:

With triethylamine; dmap; In dichloromethane; for 0.75h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00033a031

Reference yield:

(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene (126798-04-7) → (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol (126798-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 40percent trifluoroacetic acid / 0.42 h / Ambient temperature

2: Et₃N / DMAP / CH₂Cl₂ / 0.75 h / Ambient temperature

With triethylamine; trifluoroacetic acid; dmap; In dichloromethane;

DOI:10.1021/jo00033a031

Reference yield:

(3aS,4S,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (89291-76-9,126874-34-8) → (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4-(acetyloxy)-2-cyclopenten-4-ol (126798-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaH / 1) DMF, 40 min, 2) DMF, r.t., 40 min

2: 82 percent / 40percent trifluoroacetic acid / 0.42 h / Ambient temperature

3: Et₃N / DMAP / CH₂Cl₂ / 0.75 h / Ambient temperature

With sodium hydride; triethylamine; trifluoroacetic acid; dmap; In dichloromethane;

DOI:10.1021/jo00033a031

upstream raw materials:

acetic anhydride

(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-2-cyclopentene-4,5-diol

benzyl bromide

(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene