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

Base Information

• Chemical Name: <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate
• CAS No.: 134756-65-3
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 134756-65-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate 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: 94.0%

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate (134756-64-2) → <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate (134756-65-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1021/ja00015a051

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate (134756-65-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / triethylamine, DMAP / CH₂Cl₂ / 1 h

2: 95 percent / NaH₂PO₄ buffer, aq. sodium azide / 144 h / electric eel acetylcholinesterase

3: imidazole / 0.5 h

4: methanolic ammonia / 48 h

5: pyridine / CH₂Cl₂ / 0.25 h

6: methanolic ammonia / 15 h

7: 91 percent / HF / acetonitrile / 9 h

With pyridine; 1H-imidazole; dmap; sodium azide; NaH₂PO₄ buffer; hydrogen fluoride; ammonia; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ja960526c

Reference yield:

<1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol (134756-62-0) → <1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate (134756-65-3)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 1H-imidazole; hydrogen fluoride; ammonia; In dichloromethane; acetonitrile;

DOI:10.1021/ja960526c

upstream raw materials:

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate

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

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

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

Downstream raw materials:

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

3,6-di-O-benzyl-(-)-allosamizoline

(1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene

C₁₆H₁₆F₃NO₅