Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Base Information

Chemical Name:Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester
CAS No.:183988-90-1
Molecular Formula:C₂₄H₃₈N₂O₅Si
Molecular Weight:462.662
Hs Code.:

Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

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

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

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

There total 11 articles about Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-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: 71.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

: 183988-90-1
Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide;
DOI:10.1021/ja960526c

Reference yield:

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

: 183988-90-1
Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Guidance literature:: Multi-step reaction with 11 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

11: 71 percent / Et₃N / dimethylformamide

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

Reference yield:

: 134756-61-9
(1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate

: 183988-90-1
Acetic acid (3aR,4S,5S,6R,6aR)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yl ester

Guidance literature:: Multi-step reaction with 10 steps

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

2: pyridine

3: methanolic ammonia

4: K₂CO₃

5: 60 percent / trifluoroacetic anhydride, Et₃N / tetrahydrofuran / -78 - 20 °C

6: 1.) MeOTf / 1.) CH₂Cl₂

7: 32 percent / CF₃CO₃H, CF₃CO₂H

8: 46 percent / aq. CF₃CO₂H / 40 °C

9: 50 percent / Et₃N / CH₂Cl₂

10: 71 percent / Et₃N / dimethylformamide

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