(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

Base Information

Chemical Name:(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol
CAS No.:183988-91-2
Molecular Formula:C₂₂H₃₆N₂O₄Si
Molecular Weight:420.624
Hs Code.:

Synonyms:(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

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Chemical Property of (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

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Technology Process of (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

There total 12 articles about (3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol 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: 99.0%

: 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

: 183988-91-2
(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

Guidance literature:: With sodium methylate; In methanol;
DOI:10.1021/ja960526c

Reference yield:

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

: 183988-91-2
(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

Guidance literature:: Multi-step reaction with 12 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

12: 99 percent / MeONa / methanol

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

Reference yield:

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

: 183988-91-2
(3aR,4S,5S,6S,6aR)-6-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

Guidance literature:: Multi-step reaction with 10 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

9: 71 percent / Et₃N / dimethylformamide

10: 99 percent / MeONa / methanol

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