127997-05-1

Usage

Uses

Used in Organic Synthesis:
Tert-butyl (4R)-4-(R)-hydroxy[(2R)-5-oxo-2,5-dihydrofuran-2-yl]methyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate is used as a synthetic intermediate for the preparation of complex organic molecules, leveraging its unique structural features and reactivity to facilitate the synthesis of target compounds.
Used in Drug Discovery:
In the pharmaceutical industry, tert-butyl (4R)-4-(R)-hydroxy[(2R)-5-oxo-2,5-dihydrofuran-2-yl]methyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate is used as a lead compound for the development of new drugs, owing to its potential to interact with biological targets through hydrogen bonding and its specific stereochemistry, which may contribute to selective binding and therapeutic effects.
Used in Material Science:
Tert-butyl (4R)-4-(R)-hydroxy[(2R)-5-oxo-2,5-dihydrofuran-2-yl]methyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate is utilized as a component in the development of new materials, where its structural attributes may influence material properties such as stability, solubility, and reactivity in various applications.

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 

Downstream Products

• 136489-92-4 (S)-tert-Butoxycarbonylamino-((2R,3R,4R,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 135086-50-9 (R)-2,2-Dimethyl-4-[(R)-((2R,3R,4R)-5-oxo-3,4-bis-trimethylsilanyloxy-tetrahydro-furan-2-yl)-trimethylsilanyloxy-methyl]-oxazolidine-3-carboxylic acid tert-butyl ester 
• 135086-52-1 (R)-2,2-Dimethyl-4-((2R,3S,4S,5S,6R)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-yl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 135086-55-4 1,2,3,4-tetra-O-acetyl-6-deoxy-6-tert-butoxycarbonylamino-α-D-glycero-D-talo-heptopyranuronic acid methyl ester 

Relevant academic research and scientific papers

Highly Stereocontrolled Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives

An extremely selective synthesis of two novel α-aminouronic acids, the enantio-pair D-10 and L-10, through the butenolide intermediates D-2 and L-2 is described.

Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives

Two enantio couples of terminal C-glycoyranosyl α-amino acids, namely the aminopyranuronic acid, L-9, D-9 and L-10, D-10, hve been synthesized from serine-derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4.The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furaose-to-pyranose ring expansion to construct the sugar skeleton with the proper stereochemistry.In our best performance, homogeneous L-9 was prepared from L-2 in four steps and 10 reactions in 20percent overall yield.

THE FOUR-CARBON ELONGATION OF THREE-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN: HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE SEVEN-CARBON α,β-UNSATURATED 2,3-DIDEOXYALDONOLACTONES

The BF3-promoted addition of 2-(trimethylsiloxy)furan to three carbon synthons derived from D- and L-glyceraldehyde, D- and L-serinal, and imines thereof furnishes C7 α,β-unsaturated 2,3-dideoxy-aldonolactone derivatives in high yield, with very high level of diastereoselection.In all the cases, compounds having 4,5-threo:5,6-erythro relative stereodisposition preferentially emerge from the reactions, accompanied by only marginal amounts of 4,5-erythro:5,6-threo epimers.An empirical rule for the rapid assignment of the configuration at C-4 (γ-carbon) of γ-substituted unsaturated and saturated β-butyrolactones is given, based upon the sign of the optical rotation values.

SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DIDEOXY-HEPT-2-ENONO-1,4-LACTONE DERIVATIVES VIA DIASTEREOSELECTIVE ADDITION OF 2-(TRIMETHYLSILOXY)FURAN TO D-GLYCERALDEHYDE AND D-SERINAL-BASED THREE-CARBON SYNTHONS

The BF3-promoted addition of 2-(trimethylsiloxy)furan to 2,3-O-isopropylidene-D-glyceraldehyde and N-t-BOC-D-serinal, and the corresponding imine derivatives gives the title seven-carbon lactones with great preference for the D-arabino diastereoisomers.