Description

(5R,6S)-Allyl 6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-7-oxo-3-((R)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (CAS: 120705-67-1) is a highly specialized β-lactam intermediate with a complex bicyclic structure, featuring a tetrahydrofuran-2-yl substituent and a tert-butyldimethylsilyl (TBS) protected hydroxyethyl group. This compound, with the molecular formula C₂₁H₃₃NO₅SSi, is designed for advanced synthetic applications in pharmaceutical research, particularly in the development of novel antibiotics and β-lactamase inhibitors. Its stereochemically defined (5R,6S) configuration and allyl ester moiety make it a versatile building block for selective modifications. Supplied as a high-purity solid (>95% by HPLC), this product is rigorously characterized by NMR, LC-MS, and elemental analysis to ensure batch-to-batch consistency. Store under inert conditions at -20°C to maintain stability.

Properties

• CAS Number: 120705-67-1
• Complexity: 729
• IUPAC Name: allyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• InChI: InChI=1S/C21H33NO5SSi/c1-8-11-26-20(24)16-17(14-10-9-12-25-14)28-19-15(18(23)22(16)19)13(2)27-29(6,7)21(3,4)5/h8,13-15,19H,1,9-12H2,2-7H3/t13-,14-,15+,19-/m1/s1
• InChI Key: MASHLNCIEFIURF-BKEDOTJMSA-N
• Exact Mass: 439.18487086
• Molecular Formula: C21H33NO5SSi
• Molecular Weight: 439.6
• SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)[C@H]3CCCO3)C(=O)OCC=C)O[Si](C)(C)C(C)(C)C
• Topological: 90.4
• Monoisotopic Mass: 439.18487086
• Synonyms: 120705-67-1, (5R,6S)-Allyl 6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-7-oxo-3-((R)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, (5R,6S)-6-[(1R)-1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2-propenyl ester, prop-2-enyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, C21H33NO5SSi, MFCD09039289, 2VX2JEC4HQ, SCHEMBL2348971, AKOS016009625, AC-1663, DS-5111, CID 12151249, CS-0157984, C71715, (5R,6S)-Allyl6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-7-oxo-3-((R)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, 2-Propen-1-yl (5R,6S)-6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, 2-propen-1-yl ester, (5R,6S)-, 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, 2-propenyl ester, (5R,6S)-, 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-7-oxo-3-(tetrahydro-2-furanyl)-, 2-propenyl ester, [5R-[3(R*),5alpha,6alpha(R*)]]-, Ally(1 inverted exclamation mark R,2 inverted exclamation mark inverted exclamation mark R,5R,6S)-6(1 inverted exclamation mark -tert-butyl dimethyl silyloxyethy)-2-(2 inverted exclamation mark inverted exclamation mark -tetrahydrofuranyl)penem-3-carboxylate

This compound serves as a critical intermediate in the synthesis of custom β-lactam antibiotics, particularly carbapenems with enhanced resistance to enzymatic degradation. Researchers utilize its TBS-protected alcohol and allyl ester groups for targeted functionalization via cross-coupling or deprotection strategies. Its stereospecific structure enables studies on structure-activity relationships in bacterial cell wall synthesis inhibition. Suitable for medicinal chemistry optimization and PROTAC conjugation due to its reactive handles.

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