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

Base Information

Chemical Name:(3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol
CAS No.:184179-65-5
Molecular Formula:C₁₆H₂₂N₂O₄
Molecular Weight:306.362
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol

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Technology Process of (3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol

There total 9 articles about (3aS,4S,5S,6S,6aR)-6-Benzyloxymethyl-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol 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: 46.0%

: 184179-67-7
((1aR,1bR,4aR,5R,5aS)-5-Benzyloxymethyl-1b,4a,5,5a-tetrahydro-1aH-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-yl)-dimethyl-amine

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

Guidance literature:: With trifluoroacetic acid; at 40 ℃;
DOI:10.1021/ja960526c

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 9 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

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

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

Guidance literature:: Multi-step reaction with 7 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

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