(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one

Base Information

Chemical Name:(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one
CAS No.:343565-20-8
Molecular Formula:C₁₉H₂₂N₂O₄
Molecular Weight:342.395
Hs Code.:

Synonyms:(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one

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

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

There total 7 articles about (1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-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: 54.0%

: 343565-27-5
benzyl (3R,5S)-3-(3-butynylcarbamoyl)-5-(hydroxymethyl)piperidine-1-carboxylate

: 343565-28-6
benzyl (3R,5S)-3-[(3-butynyl)carbamoyl]-5-formylpiperidine-1-carboxylate

: 343565-20-8
(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-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:

: 206554-22-5
(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester

: 343565-20-8
(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: KMnO₄ / 2-methyl-propan-2-ol; aq. phosphate buffer / 1 h / 20 °C / pH 7.2

2: 80 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

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

4: 54 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

5: 125 mg / K₂CO₃ / methanol / 1 h / Heating

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

Reference yield:

: 206761-38-8
(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

: 343565-20-8
(1R,4ζ,5S)-7-benzyloxycarbonyl-3-(3-butyn-1-yl)-4-hydroxy-3,7-diazabicyclo[3.3.1]nonan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 0.25 h / -60 °C

1.2: 2.7 g / triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

2.1: KMnO₄ / 2-methyl-propan-2-ol; aq. phosphate buffer / 1 h / 20 °C / pH 7.2

3.1: 80 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

4.1: 98 percent / NaOH / methanol / 24 h / 20 °C

5.1: 54 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

6.1: 125 mg / K₂CO₃ / methanol / 1 h / Heating

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