Structure of Fmoc-Thr-Obzl
CAS No.: 73724-48-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 73724-48-8 |
| Formula : | C26H25NO5 |
| M.W : | 431.48 |
| SMILES Code : | C[C@@H](O)[C@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(OCC4=CC=CC=C4)=O |
| MDL No. : | MFCD11505901 |
| InChI Key : | WQYIETDVEJEHCP-OSPHWJPCSA-N |
| Pubchem ID : | 10950076 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

[ 73724-48-8 ]
[ 73891-07-3 ]
[ 73724-48-8 ]
[ 73891-04-0 ]

[ 73724-48-8 ]

[ 73724-48-8 ]
[ 5158-64-5 ]


[ 73724-48-8 ]
[ 572-09-8 ]

[ 191849-79-3 ]

[ 73724-48-8 ]
[ 185811-40-9 ]

[ 73724-48-8 ]

[ 213331-76-1 ]
[ 73724-48-8 ]


[ 282736-09-8 ]
[ 73724-48-8 ]



[ 73724-48-8 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride;Pd/O; | caproyl chloride is reacted with the Evans valine-derived oxazolidinone, (R)-4-isopropyloxazolidin-2-one, and n-butylLi (Step a). The resulting adduct (2) is reacted by aldol condensation with a chiral aldehyde derived from (S)-(-)-lactic acid (3) in the presence of dibutyl-BOTf and triethylamine (Step b). The 4-hydroxyl group of the resulting adduct (4) is protected as a t-butyldimethylsilyl ether (using TBS chloride and DIEA), followed by peroxide-mediated hydrolysis (using hydrogen peroxide and lithium hydroxide) of the chiral auxiliary to yield the differentially protected dihydroxy pentanoic acid (5) (Steps c and d). Differential protection of the two secondary alcohols allows for the incorporation of various carboxylic acids at the 3 position of the lactone. The carboxylic acid is coupled to N-FMOC-L-threonine benzyl ester with BOP-chloride and DMAP (Step e). Removal of the two benzyl protecting groups with H2 and Pd/O will yield the dilactone seco-acid (6) (Step f). Lactonization occurs using a BOP-Cl mediated ester-forming reaction with DMAP (Step g). Diethylamine is used to remove the FMOC protecting group to yield the dilactone (7) (Step h). N-formyl-3-amine salicylic acid is coupled to the dilactone using standard carbodiimide chemistry (Step i). In particular, the dilactone is combined with N-formyl-3-aminosalicylic acid using EDCl and HOBT, followed by treatment with TBAF. The final elaboration of the derivatized antimycin A3 structure is accomplished by fluoride-mediated removal of the silyl protecting group and coupling of the desired acid chloride (e.g., isobutyryl chloride and DIEA) (Steps j and k). |

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