benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

Base Information

Chemical Name:benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide
CAS No.:666174-91-0
Molecular Formula:C₁₆H₁₈BrNO₆S
Molecular Weight:432.292
Hs Code.:

Synonyms:benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

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Chemical Property of benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

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Technology Process of benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

There total 5 articles about benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide 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: 23.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 76454-54-1
benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide

: 666174-91-0
benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

Guidance literature:: benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide; With methylmagnesium chloride; In tetrahydrofuran; at -70 - 20 ℃; for 1h;

formaldehyd; at -70 ℃; for 6h;

Reference yield:

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 76454-54-1
benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide

: 666174-91-0
benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

: C₁₅H₁₆BrNO₅S

: benzyl (2S,5R,6R)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

Guidance literature:: With methylmagnesium chloride; In tetrahydrofuran; toluene; at -45 - 115 ℃; Inert atmosphere; Large scale;
DOI:10.1021/op050047a

Reference yield:

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

: 666174-91-0
benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide

Guidance literature:: Multi-step reaction with 2 steps

1: sodium iodide; potassium carbonate / 48 h / 30 - 40 °C / Inert atmosphere; Large scale

2: methylmagnesium chloride / toluene; tetrahydrofuran / -45 - 115 °C / Inert atmosphere; Large scale

With methylmagnesium chloride; potassium carbonate; sodium iodide; In tetrahydrofuran; toluene;
DOI:10.1021/op050047a