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

Base Information

• Chemical Name: (1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate
• CAS No.: 134756-61-9
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 134756-61-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate 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: 92.0%

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) + acetic anhydride (108-24-7) → (1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate (134756-61-9)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2005.08.061

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-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate (134756-61-9) → Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester (174810-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaH₂PO₄ buffer, aq. sodium azide / 144 h / electric eel acetylcholinesterase

2: imidazole / 0.5 h

With 1H-imidazole; sodium azide; NaH₂PO₄ buffer;

DOI:10.1021/ja960526c

upstream raw materials:

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

acetic anhydride

Downstream raw materials:

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

(+)-(1α,2β,3α)-1-acetoxy-2-<(phenylmethoxy)methyl>cyclopent-4-en-3-ol

<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

Refernces

• 1、 Griffith, David A.,Danishefsky, Samuel J.. "The total synthesis of allosamidin. Expansions of the methodology of azaglycosylation pursuant to the total synthesis of allosamidin. A surprising enantiotopic sense for a lipase-induced deacetylation". . p. 9526 - 9538. Retrieved 2007/10/03.