(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

Base Information

Chemical Name:(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one
CAS No.:343565-19-5
Molecular Formula:C₂₂H₃₂N₂O₄Si
Molecular Weight:416.593
Hs Code.:

Synonyms:(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

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Chemical Property of (1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

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Technology Process of (1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

There total 9 articles about (1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one 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: 62.0%

: 343565-24-2
benzyl (3R,5S)-5-hydroxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate

: 343565-25-3
benzyl (3R,5S)-5-formyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate

: 343565-19-5
(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6

Reference yield:

: 109720-67-4
(Z)-4-(trimethylsilyl)-3-buten-1-ylamine

: 343565-19-5
(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

2: 98 percent / NaOH / methanol / 24 h / 20 °C

3: 62 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

4: 69 mg / K₂CO₃ / methanol / 1 h / Heating

With sodium hydroxide; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; dicyclohexyl-carbodiimide; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6

Reference yield:

: 87682-62-0
(Z)-4-(trimethylsilyl)but-3-enyl 4-methylbenzene sulfonate

: 343565-19-5
(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / liq. NH₃ / tetrahydrofuran / 24 h / 20 °C / in sealed tube

2: 85 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

3: 98 percent / NaOH / methanol / 24 h / 20 °C

4: 62 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

5: 69 mg / K₂CO₃ / methanol / 1 h / Heating

With sodium hydroxide; ammonia; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6