beta-Methyl vinyl phosphate (MAP)

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Cat Number

INT90776593

CAS Number

90776-59-3

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Product Detail Description Scientific Support Customer Q&A

CAS Number

90776-59-3

EINECS

618-646-2

Storage

Store at 2-8 ℃

Synonyms

(4R,5R,6S)-3-[(Diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (4-Nitrophenyl)methyl Ester

Molecular Formula

C29H27N2O10P

Molecular Weight

594.51

Smiles

N12[C@@]([H])([C@@H]([C@H](O)C)C1=O)[C@@H](C)C(OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O)=C2C(OCC1=CC=C([N+]([O-])=O)C=C1)=O

Appearance

White solid

Melting Point

129-131 ℃

pKa

14.36±0.20

General Description

beta-Methyl vinyl phosphate (MAP) is a critical phosphate ester compound and a high-value pharmaceutical intermediate. This advanced intermediate is structurally essential for the synthesis of antibiotics in the Penem (Carbapenem) class, serving as a key precursor in the manufacturing process.

Application

MAP is a fundamental pharmaceutical intermediate for the preparation of advanced antibiotics, notably the Penem drugs, thereby supporting the production of next-generation antibacterial agents. Additionally, as a phosphate ester, it is broadly employed in chemical and biological research where it serves as a critical substrate for phosphorylation reactions necessary for investigating and understanding essential protein functions and cellular signaling pathways.

The MAP (β-methyl vinyl-phosphate meropenem precursor) strategy streamlines the construction of C-2-modified carbapenems. After mild deprotection of alkyne-terminated thioacetates, free thiol is generated with TCEP and directly reacted with MAP at −10 ℃. Michael addition displaces the vinyl-phosphate in one step to deliver protected alkyne-Carbapenemes 23 or 25 in 36–39% yield. These intermediates are stable, chromatographable and serve as universal scaffolds for copper-catalysed azide–alkyne cyclo-addition, enabling rapid assembly of triazole-linked conjugates such as 24 and 26 that merge the antibiotic core with an indole-2-carboxylate metallo-β-lactamase inhibitor. Global hydrogenolysis then removes the PNZ/PNB protecting groups to furnish the target hybrids 5 and 6.

Fig. 1 MAP for the synthesis of carbapenems. (Gao M L.; et al. 2024)