167074-37-5

Basic information

• Product Name: 2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS NO: 167074-37-5
• Molecular Formula: C13H14O4
• Molecular Weight: 234.24786
• Mol File: 167074-37-5.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol(167074-37-5)
• EPA Substance Registry System: 2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol(167074-37-5)

Safety Data

• Hazardous Substances Data: 167074-37-5(Hazardous Substances Data)

Upstream product

• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 13035-39-7 1-deoxy-D-glucopyranoside 
• 67-56-1 methanol 
• 63598-38-9 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 77453-77-1 1,5-anhydro-3-O-benzoyl-4,6-benzylidene-2-deoxy-D-arabino-hex-1-enitol 
• 66183-24-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-erythro-hex-3-ulo-1-enitol 
• 77481-85-7 1,5-anhydro-3-O-benzoyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol 
• 78-94-4 methyl vinyl ketone 
• 107-13-1 acrylonitrile 
• 80-62-6 methacrylic acid methyl ester 
• 63598-36-7 4,6-O-benzylidene-D-glucal 
• 124-41-4 sodium methylate 

Downstream Products

• 63598-36-7 4,6-O-benzylidene-D-glucal 
• 77453-78-2 1-O-benzoyl-4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranose 
• 77977-07-2 1-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranose 
• 77977-08-3 1-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-ribo-hexopyranose 
• 1380673-17-5 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-O-benzylidene-D-glucal 
• 135192-34-6 O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 
• 1563177-99-0 C₂₆H₂₆O₇ 
• 1394382-11-6 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-D-glucal 
• 74708-02-4 3-O-Acetyl-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 
• 63598-38-9 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 

Relevant articles and documents

A new entry to 4,6-O-benzylidene glucal from phenyl 1-seleno-α-d- mannopyranoside

The two-step synthesis of 4,6-O-benzylidene glucal, in 59% overall yield, from phenyl 1-seleno-α-d-mannopyranoside is described.

A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.