203515-75-7

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 203515-59-7 (4S,5R,6R)-6-(4-benzyloxybutyl)-5-methyl-4-(tert-butyldimethylsiloxy)-2-phenylsulfone-tetrahydro-2H-pyran 
• 203515-66-6 (4S,2R,3R)-4-triethylsiloxy-3-methyl(3,4-dihydro-2H-pyran-2-yl) benzotriazolyl ketone 
• 203515-46-2 ((4S,2R,3R)-4-triethylsiloxy-3-methyl(3,4-dihydro-2H-pyran-2-yl))(phenylmethoxy)methane 
• 246510-39-4 (4S,2R,3R)-4-triethylsiloxy-3-methyl-3,4-dihydro-2H-pyran-2-carboxylic acid 
• 203515-55-3 (4S,5R,6R)-6-(but-3-enyl)-5-methyl-4-(tert-butyldimethylsiloxy)-2-methoxy-tetrahydro-2H-pyran 
• 203515-65-5 (2R,3S,4S)-3-Methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-carbaldehyde 
• 203515-57-5 (4S,5R,6R)-6-(4-hydroxy-butyl)-5-methyl-4-(tert-butyldimethylsiloxy)-2-methoxy-tetrahydro-2H-pyran 
• 246510-26-9 (4S,5R,6R)-6-(3-butenyl)-5-methyl-4-hydroxy-2-methoxy-tetrahydro-2H-pyran 
• 994-30-9 triethylsilyl chloride 
• 203515-73-5 (2R,3S,4S)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-phenylsulfone-3-methyl-2-(4-benzyloxybutyl)-2H-pyran 
• 203515-74-6 (2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-(oxo)methyl] tetrahydro-6-methoxy-3-methyl-2-(4-benzyloxybutyl)-2H-pyran 

Downstream Products

• 203515-76-8 (2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(S)-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-yl] (triethylsiloxy)methyl] tetrahydro-6-methoxy-3-methyl-2-(4-benzyloxybutyl)-2H-pyran 
• 203515-78-0 C₅₅H₁₀₂O₉Si₄ 
• 203515-77-9 (1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane 

Relevant academic research and scientific papers

Enantioselective total synthesis of altohyrtin C (spongistatin 2)

The first total synthesis of a spongipyran macrolide, altohytrin C, is described. The convergent synthesis strategy relies on a regioselective macrolactonization, a stereoselective Wittig coupling of the two major synthetic fragments, a complex anti aldol reaction to join the C1-C15 and C16-C28 spiroketal regions, and an anomeric sulfone acylation to join the C29-C37 and C38-C43 pyran regions. The incorporation of the C44- C51 sidechain in the final stages of the synthesis establishes a viable route for the construction of variants in this pharmacologically important region. Methodological developments en route to the total synthesis include a 1,5 antiselective methyl ketone aldol reaction and a diastereoselective approach to Lewis acid mediated β-C-glycosidation. Completion of the synthesis has confirmed the stereochemical assignments proposed in the altohyrtin series and has established the identity of the altohyrtin and spongistatin marine macrolides.

Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF-Bis(pyran) Subunit

Keywords: altohyrtin; antitumor agents; natural products; spongistatin; total synthesis