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

Base Information

• Chemical Name: <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate
• CAS No.: 134756-64-2
• Molecular Formula: C₂₀H₃₁NO₄Si
• Molecular Weight: 377.556
• Mol file: 134756-64-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate 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:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate (134756-64-2)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja960526c

Reference yield:

(1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate (134756-61-9) → <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate (134756-64-2)

Guidance literature:

Multi-step reaction with 5 steps

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

2: imidazole / 0.5 h

3: methanolic ammonia / 48 h

4: pyridine / CH₂Cl₂ / 0.25 h

5: methanolic ammonia / 15 h

With pyridine; 1H-imidazole; sodium azide; NaH₂PO₄ buffer; ammonia; In dichloromethane;

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,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol carbamate (134756-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / 0.5 h

2: methanolic ammonia / 48 h

3: pyridine / CH₂Cl₂ / 0.25 h

4: methanolic ammonia / 15 h

With pyridine; 1H-imidazole; ammonia; In dichloromethane;

DOI:10.1021/ja960526c

upstream raw materials:

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

phenyl chloroformate

(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

Downstream raw materials:

<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

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