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

Base Information

Chemical Name:[(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate-4,4-dioxide
CAS No.:666174-87-4
Molecular Formula:C₁₈H₂₁NO₈S
Molecular Weight:411.433
Hs Code.:

Synonyms:[(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-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 [(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-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 [(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-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 [(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-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: 68.0%

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

: [(1R)-1-benzoyloxy]-ethyl-(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

: 666174-87-4
[(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate-4,4-dioxide

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tributylgermanium hydride; In acetonitrile; stereoselective reaction; Reflux;
DOI:10.1021/op050151s

Reference yield: 40.0%

: 666174-90-9
(S)-1-chloroethyl benzoate

: sodium 6β-(hydroxymethyl)penicillanate acid sulfone

: 666174-87-4
[(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate-4,4-dioxide

Guidance literature:: With 1-methyl-pyrrolidin-2-one; at 48 - 52 ℃; for 24h; Inert atmosphere; Large scale;
DOI:10.1021/op050047a

Reference yield:

: 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

: 666174-87-4
[(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-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 4 steps

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

2: N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; hydrogen / ethyl acetate; isopropyl alcohol / 1500.15 - 5250.53 Torr / Inert atmosphere; Large scale

3: sodium 2-ethylhexanoic acid / ethyl acetate / 2 h / 25 °C / Inert atmosphere; Large scale

4: 1-methyl-pyrrolidin-2-one / 24 h / 48 - 52 °C / Inert atmosphere; Large scale

With 1-methyl-pyrrolidin-2-one; palladium on activated charcoal; hydrogen; methylmagnesium chloride; N-ethyl-N,N-diisopropylamine; sodium 2-ethylhexanoic acid; In tetrahydrofuran; ethyl acetate; isopropyl alcohol; toluene;
DOI:10.1021/op050047a