81577-69-7

Basic information

• Product Name: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-phenyl-, (2R,4R,5R)-
• Synonyms: 5(R)-hydroxy-2(R)-phenyl-[1,3]dioxane-4-(R)-carbaldehyde;(2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxane-4-carbaldehyde;2,4-O-Benzyliden-D-erythrose;2,4-Benzylidene-D-erythrose;2,4-O-Benzylidene-D-erythrose;O2,O4-((R)-benzyliden)-D-erythrose;(2R,4R,5R)-5-Hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde
• CAS NO: 81577-69-7
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Mol File: 81577-69-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-phenyl-, (2R,4R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-phenyl-, (2R,4R,5R)-(81577-69-7)
• EPA Substance Registry System: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-phenyl-, (2R,4R,5R)-(81577-69-7)

Safety Data

• Hazardous Substances Data: 81577-69-7(Hazardous Substances Data)

Upstream product

• 61453-84-7 O⁴,O⁶-((R)-benzylidene)-D-glucitol 
• 3006-41-5 4,6-O-benzylidene-D-glucose 
• 104022-77-7 4,6-O-benzylidene-β-D-glucopyranosyl 
• 83212-64-0 (2R,3R)-2,3-Dihydroxy-3-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-propionaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 501373-19-9 (E)-(2R,4S,5R)-3-(5-hydroxy-2-phenyl-[1,3]dioxane-4-yl)-acrylic acid ethyl ester 
• 501373-20-2 (Z)-3-(5-(R)-hydroxy-2-(R)-phenyl-[1,3]dioxan-4-(S)-yl)acrylic acid ethyl ester 
• 501427-54-9 4-(S)-(dimethyl-hydrazonomethyl)-2-(R)-phenyl-[1,3]dioxan-5-(R)-ol 
• 951787-36-3 1,1-dibenzyl-2-(((2R,4S,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)methylene)hydrazine 
• 1017241-71-2 (2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxane-4-carboxamide 
• 653565-47-0 methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate 

Relevant articles and documents

(3: S,4 R)-3,4-Dihydroxy-N-Alkyl-l-homoprolines: Synthesis and computational mechanistic studies

This is the first synthetic report of (3S,4R)-dihydroxy-N-Alkyl-l-homoprolines described so far. 2,4-O-Benzylidene-d-erythrose was obtained from d-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-Alkyl-l-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-lactone intermediates was studied by computational means either under acidic or basic conditions. The theoretical mechanism studies fully explain the experimental results: (a) an equilibrium between l-homoprolines and their bicyclic counterparts is established in acids; (b) the equilibrium suffers a complete displacement towards the l-homoproline side in a basic medium.

Effects of α-alkoxy substitution and conformational constraints on 6-exo radical cyclizations of hydrazones via reversible thiyl and stannyl additions

Access to multifunctional hydrazones of relevance to dysiherbaine synthesis studies is described. Subsequent radical cyclizations of multifunctional hydrazones via a Si- and C-linked tethering strategy are shown to function effectively in 6-exo fashion. C

Stereochemical control in radical cyclization routes to N-glycosides: Role of protecting groups and of the configuration (E versus Z) of the acceptors

The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl or exo-hept-6-enyl type radical cyclization when a suitable radical acceptor (e.g. α,β-unsaturated este