57690-62-7

Basic information

• Product Name: METHYL 3,4-DI-O-ACETYL-D-GLUCURONAL
• Synonyms: METHYL 3,4-DI-O-ACETYL-D-GLUCURONAL;1,5-Anhydro-2-deoxy-D-arabino-hex-5-enonic acid diacetate;Methyl 3,4-di-O-acetyl-D-glucuronal min. 99%
• CAS NO: 57690-62-7
• Molecular Formula: C₁₁H₁₄O₇
• Molecular Weight: 258.23
• Mol File: 57690-62-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 329 °C at 760 mmHg
• Flash Point: 143.2 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 0.000183mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: METHYL 3,4-DI-O-ACETYL-D-GLUCURONAL(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3,4-DI-O-ACETYL-D-GLUCURONAL(57690-62-7)
• EPA Substance Registry System: METHYL 3,4-DI-O-ACETYL-D-GLUCURONAL(57690-62-7)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 57690-62-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O7/c1-6(12)17-8-4-5-16-10(11(14)15-3)9(8)18-7(2)13/h4-5,8-10H,1-3H3/t8-,9+,10+/m1/s1

Upstream product

• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 67-56-1 methanol 
• 63-29-6 D-glucurono-6,3-lactone 
• 108-24-7 acetic anhydride 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 82228-14-6 methyl D-glucopyranuronate 
• 63-29-6 (+)-D-Glucofuranurono-6,3-lacton 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 95530-80-6 methyl 1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 252000-90-1 methyl (3,4-di-O-tert-butyldimethylsilyl-D-glucuronate)glycal 
• 15910-11-9 1,4-diacetoxy 1,3-butadiene 
• 922-68-9 Methyl glyoxylate 

Downstream Products

• 90763-01-2 (2S,3R,4S)-3,4-Diacetoxy-6-((2R,3R,4R,6S)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-5-iodo-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 100603-98-3 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-α-D-mannopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose 
• 100603-97-2 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose 
• 211684-58-1 (2S,3S,6S)-3-Acetoxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-3,6-dihydro-2H-pyran-2-carboxylic acid methyl ester 
• 398460-16-7 (+)-(1S,4S,5S)-methyl 4-O-acetyl-1-O-benzyl-2,3-dideoxyhex-2-enopyranuronate 
• 351900-97-5 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 850004-42-1 O-trichloroacetimidoyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-α-D-glucuronate 
• 850004-60-3 O-4-methoxybenzyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 351900-92-0 O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 
• 351900-96-4 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 
• 351900-98-6 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzoyl-β-D-xylosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 616861-53-1 methyl (3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-(allyl 3,4-di-O-methoxymethyl-β-D-glucopyranosid)uronate 

Relevant articles and documents

Improved and large-scale synthesis of different protected d-glucuronals

Although different protected d-glucuronals are used as precursors for the preparation of many compounds, standard procedures and large-scale syntheses are still not described in the literature. In the course of the development of different protected d-glucuronyl donors we developed several versatile methods that can be used for fast and reproducible preparation of large amounts of the key intermediates. d-Glucuronolactone was converted to methyl 3,4-di-O-acetyl-d-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-d-glucal was used as starting material for an improved preparation of benzyl protected d-glucuronal, which significantly accelerates and simplifies similar methods described in the literature.

X-ray diffraction and high-resolution NMR spectroscopy of methyl 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-1-enopyranuronate

Single-crystal X-ray diffraction and high-resolution 1H and 13C NMR spectral data for methyl 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-d-arabino-hex-1-enopyranuronate are reported. The 5H4 conformation was found to be the preferred form for this glycal, both in the crystal lattice and in solution. The factors determining the 4H5 ? 5H4 conformational equilibrium for acetylated glycals are discussed.

Synthesis of 1α-Hydroperoxy Sugar Derivatives

The title compounds 4 and 5 can be prepared from acetylated glycals with H2O2 under acid catalysis.