2774-22-3

Basic information

• Product Name: Acetic acid (4aR,6R,7S,8S,8aR)-7-acetoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS NO: 2774-22-3
• Molecular Weight: 366.368
• Mol File: 2774-22-3.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: Acetic acid (4aR,6R,7S,8S,8aR)-7-acetoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (4aR,6R,7S,8S,8aR)-7-acetoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester(2774-22-3)
• EPA Substance Registry System: Acetic acid (4aR,6R,7S,8S,8aR)-7-acetoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester(2774-22-3)

Safety Data

• Hazardous Substances Data: 2774-22-3(Hazardous Substances Data)

Upstream product

• 27994-50-9 Methyl 4,6-O-Benzylidene-β-D-manno-pyranoside 
• 108-24-7 acetic anhydride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 75-36-5 acetyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 110-86-1 pyridine 

Downstream Products

• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2872-56-2 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 29868-43-7 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside 
• 56543-18-1 methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-glucopyranoside 
• 51785-62-7 Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 162284-50-6 methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 18929-80-1 methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 1384472-24-5 C₁₈H₂₄O₈ 
• 1214746-77-6 methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-mannopyranoside 
• 1214746-75-4 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-mannopyranoside 
• 205755-06-2 Succinic acid mono-{(2R,3R,4S,5R,6S)-4,5-diacetoxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-tetrahydro-pyran-3-yl} ester 
• 477949-33-0 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group

The benzylidene acetal group is one of the most important protecting groups not only in carbohydrate chemistry but also in general organic chemistry. In the case of 4,6-O-benzylidene glycosides, we previously found that the stereochemistry at 4-position altered the reaction rate constant for hydrolysis of benzylidene acetal group. However, a detail of the acceleration or deceleration factor was still unclear. In this work, the hydrolysis reaction of benzylidene acetal group was analyzed using the Arrhenius and Eyring plot to obtain individual parameters for glucosides (Glc), mannosides (Man), and galactosides (Gal). The Arrhenius and Eyring plot indicated that the pre-exponential factor (A) and ΔS? were critical for the smallest reaction rate constant of Gal among nonacetylated substrates. On the other hand, both Ea/ΔH? and A/ΔS? were influential for the smallest reaction rate constant of Gal among diacetylated substrates. All parameters obtained suggested that the rate constant for hydrolysis reaction was regulated by protonation and hydration steps along with solvation. The obtained parameters support wide use of benzylidene acetal group as orthogonal protection of cis- and trans-fused bicyclic systems through the fast hydrolysis of the trans-fused benzylidene acetal group.

Diisopropylethylamine-triggered, highly efficient, self-catalyzed regioselective acylation of carbohydrates and diols

A diisopropylethylamine (DIPEA)-triggered, self-catalyzed, regioselective acylation of carbohydrates and diols is presented. The hydroxyl groups can be acylated by the corresponding anhydride in MeCN in the presence of a catalytic amount of DIPEA. This method is comparatively green and mild as it uses less organic base compared with other selective acylation methods. Mechanistic studies indicate that DIPEA reacts with the anhydride to form a carboxylate ion, and then the carboxylate ion could catalyze the selective acylation through a dual H-bonding interaction.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.