133604-08-7

Basic information

• Product Name: (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol
• Synonyms: (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol
• CAS NO: 133604-08-7
• Molecular Weight: 396.527
• Mol File: 133604-08-7.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol(133604-08-7)
• EPA Substance Registry System: (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol(133604-08-7)

Safety Data

• Hazardous Substances Data: 133604-08-7(Hazardous Substances Data)

Upstream product

• 128632-65-5 (R)-4-((E)-(1S,2S)-1-Benzyloxy-5-bromo-2-methyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane 
• 100-52-7 benzaldehyde 
• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 
• 120040-77-9 (2R,3S)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde 
• 133604-43-0 (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-en-1-ol 
• 133604-42-9 (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid ethyl ester 

Downstream Products

• 133604-49-6 (2R,3S,4S,5S,6R)-3-Benzyloxy-4-methyl-6-phenyl-5-vinyl-hexane-1,2,6-triol 

Relevant articles and documents

A mechanistic study of the Hiyama-Nozaki allylation: Evidence for radical intermediates

A novel mechanism is suggested for the Nozaki-Hiyama allylation of aldehydes. The key intermediate is a chromium complex containing an allylic radical and the carbonyl component, from which the allylic radical may escape and undergo separate reactions. In course of chromium(II) mediated additions of relatively complex allylic bromides to aldehydes (Hiyama-Nozaki allylation) radical intermediates have been observed. From these findings a new mechanism of the allylation is derived.

Highly Felkin-Anh Selective Hiyama Additions of Chiral Allylic Bromides to Aldehydes. Application to the First Synthesis of Nephromopsinic Acid and Its Enantiomer

The chromium(II)-mediated addition ("Hiyama reaction") of the chiral allylic bromides 13, 15, 19, 22, 24, and 27 to achiral and chiral aldehydes proceeds with high Felkin-Anh selectivity with respect to the stereocenter at Cγ in the bromide (Table II). By