(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

Base Information

Chemical Name:(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine
CAS No.:444988-63-0
Molecular Formula:C₂₂H₃₃NO₅Si
Molecular Weight:419.593
Hs Code.:

Synonyms:(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

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Chemical Property of (1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

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Technology Process of (1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

There total 5 articles about (1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine 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: 58.0%

: 444988-59-4
(2S,3S,4R)-3-benzyloxy-4-tert-butyldimethylsiloxy-2,N-bis(methoxycarbonylmethyl)-pyrrolidine

: 444988-63-0
(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00005-4

Reference yield:

: 220875-15-0
(5S,6S,7R)-1,2-diaza-6-benzyloxy-7-hydroxy-3-oxo-[3.3.0]bicyclooctane

: 444988-63-0
(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

Guidance literature:: Multi-step reaction with 5 steps

1: aq. Raney nickel / 1.5 h / 20 °C / pH 7

2: HCl / 4 h

3: 0.23 g / imidazole / acetonitrile / 20 °C

4: 86 percent / Et₃N / tetrahydrofuran / 5 h / 20 °C

5: 58 percent / NaN((TMS)2 / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium hexamethyldisilazane; nickel; triethylamine; In tetrahydrofuran; acetonitrile; 5: Dieckmann condensation;
DOI:10.1016/S0040-4020(02)00005-4

Reference yield:

: 220875-27-4
2-((2S,3S,4R)-3-Benzyloxy-4-hydroxy-pyrrolidin-2-yl)-acetamide

: 444988-63-0
(1S,2R,5S,7aS)-1-benzyloxy-2-tert-butyldimethylsiloxy-5-methoxycarbonyl-6-oxo-pyrrolizidine

Guidance literature:: Multi-step reaction with 4 steps

1: HCl / 4 h

2: 0.23 g / imidazole / acetonitrile / 20 °C

3: 86 percent / Et₃N / tetrahydrofuran / 5 h / 20 °C

4: 58 percent / NaN((TMS)2 / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; acetonitrile; 4: Dieckmann condensation;
DOI:10.1016/S0040-4020(02)00005-4