Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Base Information

Chemical Name:Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester
CAS No.:183988-89-8
Molecular Formula:C₁₈H₂₄N₂O₅
Molecular Weight:348.399
Hs Code.:

Synonyms:Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

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Chemical Property of Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

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Technology Process of Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

There total 10 articles about Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl 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: 30.0%

: 108-24-7
acetic anhydride

: 184179-65-5
(3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol

: 183988-89-8
Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

: Acetic acid (3aR,4S,5S,6R,6aR)-5-acetoxy-6-benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-4-yl ester

Guidance literature:: With triethylamine; In dichloromethane;
DOI:10.1021/ja960526c

Reference yield:

: 100021-11-2
(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

: 183988-89-8
Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Guidance literature:: Multi-step reaction with 10 steps

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

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

3: pyridine

4: methanolic ammonia

5: K₂CO₃

6: 60 percent / trifluoroacetic anhydride, Et₃N / tetrahydrofuran / -78 - 20 °C

7: 1.) MeOTf / 1.) CH₂Cl₂

8: 32 percent / CF₃CO₃H, CF₃CO₂H

9: 46 percent / aq. CF₃CO₂H / 40 °C

10: 50 percent / Et₃N / CH₂Cl₂

With pyridine; dmap; sodium azide; trifluoroacetyl peroxide; NaH₂PO₄ buffer; ammonia; potassium carbonate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja960526c

Reference yield:

: 134756-62-0
<1(S)-(1α,4α,5β)>-4-(acetyloxy)-5-<(benzyloxy)methyl>-2-cyclopenten-1-ol

: 183988-89-8
Acetic acid (3aS,4S,5S,6R,6aR)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: methanolic ammonia

3: K₂CO₃

4: 60 percent / trifluoroacetic anhydride, Et₃N / tetrahydrofuran / -78 - 20 °C

5: 1.) MeOTf / 1.) CH₂Cl₂

6: 32 percent / CF₃CO₃H, CF₃CO₂H

7: 46 percent / aq. CF₃CO₂H / 40 °C

8: 50 percent / Et₃N / CH₂Cl₂

With pyridine; trifluoroacetyl peroxide; ammonia; potassium carbonate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja960526c