149198-97-0

Basic information

• Product Name: 3,4,6-tri-O-pivaloyl-D-glucal
• CAS NO: 149198-97-0
• Molecular Weight: 398.497
• Mol File: 149198-97-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-pivaloyl-D-glucal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-pivaloyl-D-glucal(149198-97-0)
• EPA Substance Registry System: 3,4,6-tri-O-pivaloyl-D-glucal(149198-97-0)

Safety Data

• Hazardous Substances Data: 149198-97-0(Hazardous Substances Data)

Upstream product

• 492-62-6 alpha-D-glucopyranose 
• 1213234-53-7 1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside 
• 3282-30-2 pivaloyl chloride 
• 108-86-1 bromobenzene 
• 1218904-46-1 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl iodide 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 113349-27-2 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside 
• 113349-30-7 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-((1S,5R)-5-isopropenyl-2-methyl-cyclohex-2-enyloxy)-tetrahydro-pyran-3,4,5-triol 
• 141206-20-4 (S)-(-)-perillyl β-D-glucopyranoside 
• 200501-84-4 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-6-((S)-4-isopropenyl-cyclohex-1-enylmethoxy)-tetrahydro-pyran-4-yl ester 
• 144448-27-1 4-Methoxyphenyl 2-deoxy-3,4,6-tri-O-pivaloyl-α-D-arabino-hexopyranoside 
• 1160753-97-8 C₂₇H₃₉N₃O₇Se 
• 1323988-39-1 (1S)-1,5-anhydro-2-deoxy-1-(2,6-dimethoxyphenyl)-3,4,6-tris-O-pivaloyl-D-erythro-hex-2-enitol 
• 1101183-45-2 C₃₅H₄₈FO₁₁P 
• 1338056-37-3 C₃₀H₄₀FO₁₀P 
• 1338056-38-4 C₃₀H₃₈FO₁₁P 
• 1336911-26-2 (2R,3S,6S)-6-cyclohexenyl-2-(pivaloyloxymethyl)-3,6-dihydro-2H-pyran-3-yl pivalate 
• 1360148-34-0 C₂₈H₃₉ClO₁₀ 
• 1360148-30-6 C₂₈H₃₉ClO₁₀ 

Relevant articles and documents

Pivaloyl-protected glucosyl iodide as a glucosyl donor for the preparation of β-C-glucosides

A method for the selective synthesis of β-C-glucosides using α-D-tetra-O-pivaloylglucosyl iodide as a glucosyl donor is reported. Its diastereoselectivity differs from that of the respective acetyl-protected glucosyl bromide, as it reported in the literature under similar reaction conditions. The concentration of the catalyst, the solvent and the type of additive used are crucial factors that determine the reaction selectivity. This method has been applied in a short synthesis of dapagliflozin. The stability of α-D-tetra-O-pivaloylglucosyl iodide in CDCl3 and THF at reflux was also studied. All side products in the coupling and decomposition reactions were isolated and characterized, and possible pathways for their formation are proposed.