201336-86-9

Upstream product

• 214533-08-1 (3R,5S)-5-(4-Methoxy-benzyloxy)-3-methyl-7-[(2S,5R)-3-methylene-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-tetrahydro-furan-2-yl]-heptanal 
• 214533-06-9 (3S,5S)-5-(4-Methoxy-benzyloxy)-3-methyl-7-[(2S,5R)-3-methylene-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-tetrahydro-furan-2-yl]-heptanenitrile 
• 214533-02-5 (2S,3S,5R)-2-<(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyhexyl>-5-(hydroxymethyl)tetrahydrofuran-3-ol 
• 157158-44-6 (5E,2R,8S,10R)-11-(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-8-(4-methoxybenzyloxy)-10-methyl-5-undecen-4-one 
• 157158-42-4 (5E,2R,4S,8S,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol 
• 214532-94-2 (2S,5R)-5-(benzoyloxymethyl)-2-<(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyhexyl>tetrahydrofuran-3-one 
• 157158-47-9 (2S,5R)-2-<(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methylhexyl>-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuran 
• 157158-46-8 (2S,3S,5R)-2-<(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyhexyl>-5-(benzoyloxymethyl)tetrahydrofuran-3-ol 
• 214533-01-4 (2S,3S,5R)-2-<(1E,3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methy-1-hexenyl>-5-(hydroxymethyl)tetrahydrofuran-3-ol 
• 214533-03-6 (2S,5R)-2-<(3S,5R)-6-hydroxy-3-(4-methoxybenzyloxy)-5-methylhexyl>-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuran 
• 214532-93-1 (3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol 
• 157158-37-7 (3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methylhexanal 
• 214533-05-8 (3S,5S)-7-((2S,5R)-5-Hydroxymethyl-3-methylene-tetrahydro-furan-2-yl)-5-(4-methoxy-benzyloxy)-3-methyl-heptanenitrile 
• 157158-36-6 (3R,5R)-6-(tert-butyldiphenylsilyloxy)-5-methylhexane-1,3-diol 

Downstream Products

• 214533-23-0 (2R,4S,5S,6R,7R,8S,10S,11S,12R,14R,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-11-hydroxymethyl-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8;17,20-diepoxyhenicosan-10-ol 
• 214533-36-5 C₄₆H₆₆O₁₂Si 
• 214533-24-1 (2R,4S,5S,6R,7R,8S,10S,11S,12R,14S,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-1,2-isopropylidenedioxy-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-11-toluenesulfonyloxymethyl-21-<2-(trimethylsilyl)ethoxymethoxy>-4,8; 17,20-diepoxyhenicosan-... 
• 201336-87-0 methyl (2R,4S,5S,6S,7R,8S,11RS,12R,14S,17S,20R)-1,2-diacetoxy-5,7-bis(tert-butyldimethylsilyloxy)-14-(4-methoxybenzyloxy)-6,12-dimethyl-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-10-oxo-4,8; 17,20-diepoxyhenicosane-11-carboxylate 
• 214533-41-2 C₆₃H₁₀₀O₁₁SSi₃ 
• 214533-38-7 (2R,4S,5S,6R,7R,8S,10R,11RS,12R,14S,17S,20R)-5,7-bis(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-11-methoxycarbonyl-6-methyl-18-methylidene-4,8; 10,14; 17,20-triepoxyhenicosane 
• 214533-39-8 C₅₆H₉₄O₉Si₃ 
• 201336-89-2 (2R,4S,5S,6R,7R,8S,10R,12R,14S,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-21-(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-6-methyl-11,18-dimethylidene-4,8; 10,14; 17,20-triepoxyhenicosane 
• 214533-33-2 benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester 
• 201336-88-1 methyl (2R,4S,5S,6R,7R,8S,10R,11RS,12R,14S,17S,20R)-1,2-diacetoxy-21-(tert-butyldiphenylsilyloxy)-5,7-dihydroxy-6-methyl-18-methylidene-4,8; 10,14; 17,20-triepoxyhenicosane-11-carboxylate 
• 214533-37-6 6-{2-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-ethyl}-2-[6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3,5-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-tetrahydro-pyran-3-carboxylic acid methyl ester 
• 214532-97-5 (2R,4S,5S,6R,7R,8S,10R,12R,14S,17S,20R)-21-benzoyloxy-1,2-isopropylidenedioxy-6-methyl-11,18-dimethylidene-4,8; 10,14; 17,20-triepoxyhenicosane-5,7-diol 
• 214533-34-3 methyl (2R,4S,5S,6S,7R,8S,11R,12R,14S,17S,20R)-5,7-bis(tert-butyldimethylsilyloxy)-1,2-isopropylidenedioxy-6,12-dimethyl-14-(4-methoxybenzyloxy)-18-methylidene-21-<2-(trimethylsilyl)ethoxymethoxy>-10-oxo-4,8; 17,20-diepoxyhenicosane-11-carboxylate 

Relevant academic research and scientific papers

Synthetic studies on halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 9. Synthesis of the C16 - C36 unit via stereoselective construction of the D and E rings

The C16 - C36 unit of halichondrin B was stereoselectively synthesized via the aldol condensation of two C16 - C26 esters with the previously synthesized C27 - C36 aldehyde followed by E ring construction. The C16 - C26 esters were prepared starting from (2S)-3-hydroxy-2-methylpropionic acid and L-tartaric acid via construction of the D ring by iodoetherification.

Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 8. Synthesis of the lactone part (C1-C36) via Horner-Emmons coupling between C1-C15 and C16-C36 fragments and Yamaguchi lactonization.

The lactone part (2) of halichondrin B (1) was synthesized by Yamaguchi macrolactonization of the seco-acid (3), which was synthesized via coupling of C1-C15 (4) with C16-C36 (5). prepared through stereoselective construction of the E ring starting from C16-C26 (7) and C27-C36 (8).