871348-24-2

Basic information

• Product Name: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose
• Synonyms: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose;Eribulin intermediate C;Eribulin intermediate ERC;2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde
• CAS NO: 871348-24-2
• Molecular Formula: C29H52O7SSi2
• Molecular Weight: 600.96
• Mol File: 871348-24-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 597.9±48.0 °C(Predicted)
• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose(871348-24-2)
• EPA Substance Registry System: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose(871348-24-2)

Safety Data

• Hazardous Substances Data: 871348-24-2(Hazardous Substances Data)

Usage

Description

3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose is a complex organic compound that serves as an intermediate in the synthesis of Eribulin mesylate (E615203), a synthetic analog of the marine natural product halichondrin B.

Uses

Used in Pharmaceutical Industry:
3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose is used as a key intermediate in the synthesis of Eribulin mesylate, a drug that has demonstrated potent anticancer activity. Its role in the production of Eribulin mesylate makes it a valuable component in the development of cancer treatments, particularly for solid tumors.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 546141-40-6 C₁₈H₂₆O₆S 
• 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 
• 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 
• 871348-10-6 (2R,3R,4R,5S)-5-allyl-2-[(S)-2,3-dihydroxypropyl]-4-[(phenylsulfonyl)methyl]tetrahydrofuran-3-ol 
• 546141-26-8 C₃₁H₃₂O₈S 
• 871348-08-2 C₃₁H₃₀O₈S 
• 871348-06-0 C₃₈H₃₆O₈S 
• 871348-04-8 [(2S)-3-[(2R,3S,5S)-5-allyl-3-benzyloxy-4-oxo-tetrahydrofuran-2-yl]-2-benzoyloxypropyl] benzoate 
• 546141-24-6 [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate 
• 871348-03-7 C₃₁H₃₂O₈ 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 871348-22-0 C₃₀H₅₄O₆SSi₂ 

Downstream Products

• 1316279-29-4 C₅₃H₈₅IO₁₂SSi₂ 
• 1316279-25-0 C₆₁H₉₁IO₁₄SSi₂ 

Relevant articles and documents

Process development of halaven: Synthesis of the C14-C35 fragment via iterative nozaki-hiyama-kishi reaction-williamson ether cyclization

Multikilogram manufacturing process of the Halaven C14-C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment. Georg Thieme Verlag Stuttgart - New York.