157322-83-3

Basic information

• Product Name: Eribulin mesylate intermediate
• Synonyms: Eribulin mesylate intermediate;Eribulin mesylate intermediate1;Eribulin intermediate ERA;L-arabino-D-allo-Tridec-12-enonic acid, 3,7:6,10-dianhydro-2,4,5,12,13-pentadeoxy-8,9,11-tris-O-[(1,1-dimethylethyl)dimethylsilyl]-13-iodo-, methyl ester, (12E)-;Eribulin intermediate A;methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis(tert-butyldimethylsilyloxy)-6-((S,E)-1-(tert-butyldimethylsilyloxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate;((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate;(12E)-3,7:6,10-Dianhydro-2,4,5,12,13-pentadeoxy-8,9,11-tris-O-[(1,1-dimethylethyl)dimethylsilyl]-13-iodo-L-arabino-D-allo-tridec-12-enonic acid methyl ester
• CAS NO: 157322-83-3
• Molecular Formula: C₃₂H₆₃IO₇Si₃
• Molecular Weight: 771
• Product Categories: Intermediates
• Mol File: 157322-83-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 608.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Eribulin mesylate intermediate(CAS DataBase Reference)
• NIST Chemistry Reference: Eribulin mesylate intermediate(157322-83-3)
• EPA Substance Registry System: Eribulin mesylate intermediate(157322-83-3)

Safety Data

• Hazardous Substances Data: 157322-83-3(Hazardous Substances Data)

Usage

Uses

Methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate, is an intermediate in the synthesis of Eribulin mesylate (E615203), a synthetic analog of the marine natural product halichondrin B.

Upstream product

• 185411-09-0 C₁₉H₃₀O₈ 
• 871360-14-4 C₁₈H₂₆O₇ 
• 871360-33-7 [(2R,4aS,6S,7S,8R,8aR)-7,8-Dihydroxy-6-((E)-(S)-1-hydroxy-3-trimethylsilanyl-allyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 185411-11-4 {(2R,4aS,6S,7R,8S,8aS)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-allyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester 
• 185411-07-8 C₂₇H₄₀O₉ 
• 185411-08-9 C₂₅H₃₈O₈ 
• 185411-06-7 C₂₃H₃₄O₉ 
• 185411-10-3 C₂₃H₃₈O₇Si 

Relevant articles and documents

PROCESS FOR PREPARATION OF ERIBULIN AND INTERMEDIATES THEREOF

The present application relate to process for preparation of octahydropyrano [3, 2-b] pyran compound of formula II, which is useful as an intermediate for the preparation of halichondrin B analogues such as Eribulin or its pharmaceutically acceptable salts.

Synthetic studies on halichondrins: A practical synthesis of the C.1-C.13 segment

A practical, scalable synthesis of the C.1-C.13 segment of halichondrin B has been developed starting from L-mannonic-γ-lactone, using C-allylation/oxy-Michael cyclization and Ni(II)/Cr(II)-mediated vinyltrimethylsilane addition to set the C.6/C.3 and C.11 stereocenters, respectively.