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Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of (3R,5R)-Rosuvastatin (R700510), a widely prescribed drug for the treatment of high cholesterol and related cardiovascular conditions. Its role in the production of this medication is crucial, as it contributes to the development of a more effective and safer treatment option for patients.
2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester is also used as an intermediate in the preparation of phorboxazole B, a compound with potential anti-cancer properties. Its involvement in the synthesis of 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester highlights its importance in the development of novel therapeutic agents for the treatment of cancer.
Furthermore, 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester is utilized in the production of bryostatin 2, a complex natural product with potential applications in the treatment of various diseases, including cancer. Its role in the synthesis of 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester underscores its significance in the development of innovative pharmaceuticals with diverse therapeutic applications.

Upstream product

• 147849-63-6 tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 146431-18-7 (Z)-1,3-bis(trimethylsiloxy)-1-tert-butoxybuta-1,3-diene 
• 540-88-5 acetic acid tert-butyl ester 
• 106058-91-7 (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate 

Downstream Products

• 296785-20-1 (2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol 
• 296785-16-5 (4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one 
• 310883-86-4 (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Enantioselective synthesis of oasomycin A, part II: Synthesis of the C29-C46 subunit

(Chemical Equation Presented) Putting the pieces together: The total synthesis of the natural macrolide oasomycin A has been realized. Key fragment couplings include an anti-Felkin selective aldol addition (green), Kociensky-Julia olefinations (red), and

Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation

The asymmetric transfer hydrogenation of chiral 5-hydroxy-3-ketoesters in 2-propanol using chlororuthenium(II)arene/β-amino alcohol in situ catalyst combinations or a pre-synthesized Ru-{β-amino alcohol} true catalyst, provides syn-3,5-dihydroxyesters in

Application of complex aldol reactions to the total synthesis of phorboxazole B

The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of 12.6%. The absolute stereochemistry of the C4-C12, C33-C38, and C13-C19 fragments was established utilizing catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20-C32 fragment was derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully elaborated alkenyl metal side chain.

Asymmetric synthesis of bryostatin 2

The potent bryostatin antitumor agents are currently in phase II clinical trials for the treatment of a variety of forms of cancer. Aldol reactions and directed reductions are among the essential steps for the formation of fragments A-C in the total synthesis of the title compound. Coupling of these fragments by sulfone-based olefination and alkylation reactions was followed by macrocyclization and introduction of the enoate moieties on rings B and C.