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

Base Information

• Chemical Name: Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester
• CAS No.: 174810-43-6
• Molecular Formula: C₂₁H₃₂O₄Si
• Molecular Weight: 376.568
• Mol file: 174810-43-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 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) → 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 3 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

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

DOI:10.1021/ja960526c

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

Reference yield:

<1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol (134756-62-0) + tert-butyldimethylsilyl chloride (18162-48-6) → Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester (174810-43-6)

Guidance literature:

With 1H-imidazole; In dichloromethane;

DOI:10.1021/ja00015a051

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

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

Downstream raw materials:

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

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