(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

Base Information

Chemical Name:(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate
CAS No.:82443-05-8
Molecular Formula:C₂₄H₂₁N₅O₅
Molecular Weight:459.461
Hs Code.:

Synonyms:(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

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Chemical Property of (9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

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Technology Process of (9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

There total 12 articles about (9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate 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:

: 82394-91-0,82443-06-9
(9RS,9aRS)-benzyl 9-amino-9,9a-dihydro-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

: 82443-06-9
(9S,9aS)-benzyl 9-amino-9,9a-dihydro-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

: 82394-94-3
(9R,9aR)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

: 82443-05-8
(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

Guidance literature:: With D-mandelic O-carboxyanhydride; In dichloromethane; at -20 ℃; for 1h; Yield given. Yields of byproduct given;
DOI:10.1039/P19850001491

Reference yield:

: 61795-31-1
benzyl 2-amino-3,3-ethylenedioxybutanoate

: 82443-05-8
(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 23 g / magnesium sulphate / CH₂Cl₂ / 16 h

2: triethylamine / CH₂Cl₂ / 1 h / 0 °C

3: tetraethylammonium fluoride / tetrahydrofuran / 0.33 h

4: 5percent trifluoroacetic acid / H₂O / 1.5 h

5: triethylamine / CH₂Cl₂ / 0 °C

6: sodium azide / dimethylformamide / 0.17 h

7: benzene / Heating

8: triethylamine, hydrogen sulphide / CH₂Cl₂ / 1 h / 0 °C

9: D-mandelic O-carboxyanhydride / CH₂Cl₂ / 1 h / -20 °C

10: CH₂Cl₂ / 3 h / -20 °C

With sodium azide; D-mandelic O-carboxyanhydride; hydrogen sulfide; tetraethylammonium fluoride; magnesium sulfate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19850001491

Reference yield:

: (3RS,4SR)-3-azido-1-(1-benzyloxycarbonyl-2,2-ethylenedioxypropyl)-4-ethynylazetidin-2-one

: 82443-05-8
(9S,9aS)-benzyl 9,9a-dihydro-9-(D-α-hydroxyphenylacetamido)-5-methyl-8-oxo-8H-azeto<1,2-a>-v-triazolo<5,1-c>pyrazine-6-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 5percent trifluoroacetic acid / H₂O / 1.5 h

2: triethylamine / CH₂Cl₂ / 0 °C

3: sodium azide / dimethylformamide / 0.17 h

4: benzene / Heating

5: triethylamine, hydrogen sulphide / CH₂Cl₂ / 1 h / 0 °C

6: D-mandelic O-carboxyanhydride / CH₂Cl₂ / 1 h / -20 °C

7: CH₂Cl₂ / 3 h / -20 °C

With sodium azide; D-mandelic O-carboxyanhydride; hydrogen sulfide; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19850001491