3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Base Information

Chemical Name:3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester
CAS No.:697290-13-4
Molecular Formula:C₂₈H₄₂N₂O₈Si
Molecular Weight:562.736
Hs Code.:

3-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-<i>a</i>]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-<i>tert</i>-butyl ester

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Chemical Property of 3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

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Technology Process of 3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

There total 5 articles about 3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl 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:

: 697289-86-4
tert-butyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)propionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

: 697290-13-4
3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Guidance literature:: With sodium periodate; In water; acetone; at 0 - 20 ℃;
DOI:10.1002/ejoc.200300700

Reference yield:

: 697289-60-4
(1S,3S,4R)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid tert-butyl ester

: 697290-13-4
3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / KMnO₄; NaOH / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

2: 70 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 760 Torr

3: 53 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

4: NaIO₄ / acetone; H₂O / 0 - 20 °C

With sodium hydroxide; potassium permanganate; sodium periodate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1002/ejoc.200300700

Reference yield:

: (1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester

: 697290-13-4
3-(tert-butyl-dimethyl-silanyloxymethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 760 Torr

2: 53 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

3: NaIO₄ / acetone; H₂O / 0 - 20 °C

With sodium periodate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.200300700