(3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one

Inquiry

Cat Number

INT866594607

CAS Number

866594-60-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

866594-60-7

EINECS

692-063-1

Storage

2-8℃

Molecular Formula

C7H10O4

Molecular Weight

158.15

Smiles

CO[C@@H]1[C@H]2CC(=O)O[C@H]2CO1

Appearance

White to off-white powder or crystals

Melting Point

126-128℃

Relative Density

1.26

General Description

(3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one is a chiral bicyclic lactone containing a fused tetrahydrofuro-furan ring system. This compound is an advanced building block for asymmetric synthesis, providing a rigid, oxygen-rich heterocyclic scaffold with defined stereochemistry and multiple functionalization sites.

Application

Used mainly as a high purity intermediate, (3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one finds application in the synthesis of complex pharmaceutical agents, particularly in the production of protease inhibitors and antiviral drugs.

Quaedflieg P J L M et al. developed two short and efficient synthetic routes to bis-THF-alcohol 2, a key intermediate for the investigational HIV protease inhibitor TMC114 (1). Both routes commence from S-2,3-O-isopropylideneglyceraldehyde (4) as the chiral source. The synthetic sequence involves a diastereoselective Michael addition of nitromethane, which predominantly yields the syn isomers 6. These are then subjected to Nef oxidation and cyclization to afford lactone acetals 8, followed by a reduction and final cyclization to deliver the target molecule 2.

Fig. 1 Application in synthesis of (3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one. (Quaedflieg P J L M.; et al. 2005)

References

Quaedflieg P J L M, et al. Stereoselective and Efficient Synthesis of (3 R, 3a S, 6a R)-Hexahydrofuro [2, 3-b] furan-3-ol. Organic Letters, 2005, 7(26): 5917-5920.

What are the main applications of (3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one?

It is used mainly for the synthesis of complex APIs.

What is the purity grade of your (3aS,4S,6aR)-4-Methoxytetrahydrofuro[3,4-b]furan-2(3H)-one?

We offer it in a high-purity grade for pharmaceutical R&D and production.

What is the lead time?

Lead times vary according to stock availability and the quantities ordered.