(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

Base Information

Chemical Name:(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone
CAS No.:1577180-36-9
Molecular Formula:C₂₄H₄₀N₂O₃Si₂
Molecular Weight:460.764
Hs Code.:

Synonyms:(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

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Chemical Property of (3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

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Technology Process of (3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

There total 1 articles about (3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone 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: 80.0%

: 7677-24-9
trimethylsilyl cyanide

: (3R,4R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-acetoxy-1-benzyl-2-pyrrolidinone

: 1577180-36-9
(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

: 1577180-37-0
(3R,4S,5S)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

Guidance literature:: With boron trifluoride diethyl etherate; In toluene; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Temperature; Time; stereoselective reaction; Inert atmosphere;
DOI:10.1002/jhet.1634

Reference yield:

: 1577180-36-9
(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

: 1577468-52-0
1-benzyl-3,4-dihydroxyproline hydrochloride

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogenchloride / 5 h / 20 °C / Cooling with ice

2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Cooling with ice

3: borane-THF / tetrahydrofuran / 20 °C / Inert atmosphere

4: hydrogenchloride / Reflux

With 1H-imidazole; hydrogenchloride; borane-THF; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/jhet.1634

Reference yield:

: 1577180-36-9
(3R,4S,5R)-1-benzyl-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-2-pyrrolidinone

: (2R,3S,4S)-2-(Hydroxymethyl)-3,4-dihydroxy-1-benzylpyrrolidine hydrochloride

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogenchloride / 5 h / 20 °C / Cooling with ice

2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Cooling with ice

3: borane-THF / tetrahydrofuran / 20 °C / Inert atmosphere

4: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere

5: hydrogenchloride / methanol / 20 °C

With 1H-imidazole; hydrogenchloride; borane-THF; diisobutylaluminium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/jhet.1634