1193375-17-5

Upstream product

• 871348-24-2 2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde 
• 157322-47-9 3-((2S,5S)-5-((3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-en-1-yl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate 
• 871348-16-2 (2R,3R,4R,5S)-5-allyl-2-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-((phenylsulfonyl)methyl)tetrahydrofuran-3-ol 
• 546141-41-7 (S)-4-(((2R,3R,4S,5S)-5-allyl-3-methoxy-4-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-2,2-dimethyl-1,3-dioxolane 
• 480444-16-4 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate 
• 1193375-14-2 C₅₂H₆₆O₁₂S 

Downstream Products

• 253128-09-5 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl) ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate 
• 253128-10-8 3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol 

Relevant academic research and scientific papers

PROCESS FOR PREPARATION OF ERIBULIN AND INTERMEDIATES THEREOF

The present application relate to a process for preparation of 4-methylene tetrahydrofuran compound of formula II, which is useful as an intermediate for the preparation of halichondrin B analogues such as eribulin and its pharmaceutically acceptable salts thereof. The present application also provide crystalline compound of formula III and crystalline compound of formula II.

Prins Reaction of Homoallenyl Alcohols: Access to Substituted Pyrans in the Halichondrin Series

Prins reaction of homoallenyl alcohols with aldehyde dimethylacetals in the presence of methoxyacetic acid directly affords tetrasubstituted pyrans relevant to halichondrins with complete control of the C27 stereogenic center. Regioselective Tsuji reducti

MACROCYCLIZATION REACTIONS AND INTERMEDIATES USEFUL IN THE SYNTHESIS OF ANALOGS OF HALICHONDRIN B

The invention provides methods for the synthesis of eribulin or a pharmaceutically acceptable salt thereof (e.g., eribulin mesylate) through a macrocyclization strategy. The macrocyclization strategy of the present invention involves subjecting a non-macrocyclic intermediate to a carbon-carbon bond-forming reaction (e.g., an olefination reaction (e.g., Horner-Wadsworth-Emmons olefination), Dieckmann reaction, catalytic Ring-Closing Olefin Metathesis, or Nozaki-Hiyama-Kishi reaction) to afford a macrocyclic intermediate. The invention also provides compounds useful as intermediates in the synthesis of eribulin or a pharmaceutically acceptable salt thereof and methods for preparing the same.

New syntheses of E7389 C14-C35 and halichondrin C14-C38 building blocks: Reductive cyclization and oxy-Michael cyclization approaches

Cr-mediated coupling reactions are usually achieved with a slight excess of a given nucleophile. To develop a cost-effective use of this process, two different approaches have been studied. The first approach depends on two consecutive catalytic asymmetri