(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

Base Information

Chemical Name:(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine
CAS No.:1443150-71-7
Molecular Formula:C₁₈H₂₈N₄O₃Si
Molecular Weight:376.531
Hs Code.:

Synonyms:(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

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Technology Process of (3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

There total 8 articles about (3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine 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: 57.0%

: 1443150-70-6
(3R,4R)-(-)-1-benzyloxycarbonyl-3-bromo-4-(tert-butyldimethylsilyloxy)pyrrolidine

: 1443150-71-7
(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: With sodium azide; In dimethyl sulfoxide; at 20 - 110 ℃; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.04.012

Reference yield:

: 31970-04-4
1-carboxybenzyl-3-pyrrolidine

: 1443150-71-7
(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: N-Bromosuccinimide; water / 4 h / 20 °C / Cooling with ice

2: potassium carbonate / acetonitrile / 12 h / 20 °C

3: water; Candida antarctica Lipase A / 24 h / 30 °C / Resolution of racemate; Enzymatic reaction

4: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

5: sodium azide / dimethyl sulfoxide / 20 - 110 °C / Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; sodium azide; Candida antarctica Lipase A; water; potassium carbonate; In dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.tetasy.2013.04.012

Reference yield:

: 1-Cbz-trans-3-bromo-4-hydroxypyrrolidine

: 1443150-71-7
(3S,4R)-(+)-1-benzyloxycarbonyl-3-azido-4-(tert-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: potassium carbonate / acetonitrile / 12 h / 20 °C

2: water; Candida antarctica Lipase A / 24 h / 30 °C / Resolution of racemate; Enzymatic reaction

3: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

4: sodium azide / dimethyl sulfoxide / 20 - 110 °C / Inert atmosphere

With 1H-imidazole; sodium azide; Candida antarctica Lipase A; water; potassium carbonate; In dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.tetasy.2013.04.012