194934-58-2

Upstream product

• 194934-56-0 (2R,3R,4R,5R)-3-benzyloxy-6-(p-methoxybenzyloxy)-5-methylhexane-2,4-diol 
• 194934-57-1 (4R,5R,6R)-5-benzyloxy-4-[1-(p-methoxybenzyloxy)-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane 
• 194934-55-9 (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone 
• 862509-84-0 (4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane 

Downstream Products

• 194934-52-6 methyl (2E,4R)-4-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pent-2-enoate 
• 194934-62-8 1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one 
• 194934-60-6 (2S,3R,4R)-4-((4R,5R,6R)-5-Benzyloxy-2,2,6-trimethyl-[1,3]dioxan-4-yl)-2,3-bis-(2-trimethylsilanyl-ethoxymethoxy)-pentanoic acid methyl ester 
• 194934-61-7 (E)-(5R,6R,7R)-7-((4R,5R,6R)-5-Benzyloxy-2,2,6-trimethyl-[1,3]dioxan-4-yl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-oct-3-en-2-one 
• 392692-65-8 C₆₃H₉₆BClO₁₁Si 
• 392692-67-0 C₆₂H₉₄Cl₂O₁₂Si₂ 
• 392692-68-1 C₆₃H₉₆Cl₂O₁₁Si₂ 
• 392692-66-9 1-[6-[[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-7-chloro-4-hydroxy-octa-5,7-dien-2-one 
• 537041-15-9 (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran 
• 392692-64-7 1-[(2R,3R,4R,5R,6R)-6-[(S)-[(2R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one 
• 392692-63-6 (2R,4S,5R,6R)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran-4-ol 
• 392692-54-5 1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one 
• 392692-62-5 (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one 
• 392692-58-9 C₄₉H₆₇BO₈ 

Relevant academic research and scientific papers

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The southern hemisphere EF segment

The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran. The Royal Society of Chemistry 2005.

Stereocontrolled total synthesis of (+)-altohyrtin A/spongistatin 1

As an exceptionally potent antimitotic macrolide, altohyrtin A/spongistatin 1 shows great promise in cancer chemotherapy but its extreme scarcity in the natural sponges has halted its further preclinical development. A highly stereocontrolled total synthe

Studies in marine macrolide synthesis: Stereocontrolled synthesis of the F-ring subunit of spongistatin 1 (Altohyrtin A).

The C36-C46 subunit 3, containing the F ring of spongistatin 1 (1), was prepared in 12 steps from ketone (R)-7. Key steps include: (i) the boron-mediated anti aldol reaction, 7 → 9; (ii) the Sharpless AD, 6 → 13; and (iii) an intramolecular hetero-Michael addition, followed by base-promoted equilibration to give 3.