14315-85-6

Basic information

• Product Name: methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside
• Synonyms: methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside
• CAS NO: 14315-85-6
• Molecular Weight: 402.401
• Mol File: 14315-85-6.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside(14315-85-6)
• EPA Substance Registry System: methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside(14315-85-6)

Safety Data

• Hazardous Substances Data: 14315-85-6(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 93-97-0 benzoic acid anhydride 
• 67381-28-6 methyl 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 67381-26-4 methyl 3,6-di-O-allyl-α-D-mannopyranoside 
• 100-47-0 benzonitrile 
• 79218-70-5 methyl 3,6-di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 90213-81-3 Methyl-3,6-di-O-benzoyl-α-D-arabino-hexopyranosid-2-ulose 
• 6605-40-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 

Downstream Products

• 129217-40-9 methyl 3,6-di-O-benzoyl-2-O-(benzoylcarbamyl)-4-O-<(trifluoromethyl)sulfonyl>-α-D-mannopyranoside 
• 129217-41-0 C₂₉H₂₅NO₉ 
• 129217-42-1 methyl 4-amino-3,6-di-O-benzoyl-4-deoxy-2,4-O,N-(internal carbamate)-α-D-talopyranoside 
• 209906-16-1 O-(3,6-Di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranosyl)trichloroacetimidate 
• 68601-72-9 methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside 
• 79218-70-5 methyl 3,6-di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 129217-46-5 C₂₉H₂₇NO₁₀ 
• 90213-81-3 Methyl-3,6-di-O-benzoyl-α-D-arabino-hexopyranosid-2-ulose 
• 101194-13-2 methyl 2,4-di-O-allyl-3,6-di-O-benzoyl-α-D-mannopyranoside 
• 80245-05-2 methyl 3,6-di-O-benzoyl-α-D-glucopyranoside 

Relevant articles and documents

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.

Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope

This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents. This journal is

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.