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

Base Information

• Chemical Name: <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol
• CAS No.: 134756-62-0
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 134756-62-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-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: 95.0%

(1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate (134756-61-9) → <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol (134756-62-0)

Guidance literature:

With sodium azide; via action of electric eel acetylcholinesterase, phosphate buffer (pH 6.9);

DOI:10.1021/ja00015a051

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → <1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol (134756-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine / 12 h / 20 °C

2: immobilized Pseudomonas cepacia lipase PS-30; phosphate buffer / H₂O; toluene / 18 h / 25 °C / pH 7.0

With pyridine; phosphate buffer; immobilized Pseudomonas cepacia lipase PS-30; In water; toluene;

DOI:10.1016/j.tetasy.2005.08.061

Reference yield:

<1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol (134756-62-0) → <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one (134875-85-7)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / 0.5 h

2: methanolic ammonia / 48 h

3: pyridine / CH₂Cl₂ / 0.25 h

4: methanolic ammonia / 15 h

5: 91 percent / HF / acetonitrile / 9 h

6: 63 percent / triethylamine, trifluoroacetic anhydride / tetrahydrofuran / 4 h / -78 - 20 °C

With pyridine; 1H-imidazole; hydrogen fluoride; ammonia; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja960526c

upstream raw materials:

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

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Downstream raw materials:

Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester

<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,6a-dihydro-N,N-dimethyl-6H-cyclopentoxazol-2-amine

<1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate