13242-55-2

Basic information

• Product Name: 1,6-ANHYDRO-BETA-D-GLUCOSE-2,3,4-TRI-O-ACETATE
• Synonyms: 1,6-ANHYDRO-2,3,4-TRI-O-ACETYL-B-D-GLUCOPYRANOSE;1,6-ANHYDRO-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSA;1,6-ANHYDRO-2,3,4-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSE;1,6-ANHYDRO-2,3,4-TRI-O-ACETYL-B-GLUCOPYRANOSE;1,6-ANHYDRO-BETA-D-GLUCOSE 2,3,4-TRIACETATE;1,6-ANHYDRO-BETA-D-GLUCOSE-2,3,4-TRI-O-ACETATE;1,6-ANHYDRO-BETA-D-GLUCOSE TRIACETATE;1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE, 2,3,4-TRIACETATE
• CAS NO: 13242-55-2
• Molecular Formula: C₁₂H₁₆O₈
• Molecular Weight: 288.25
• EINECS: 236-222-1
• Product Categories: Sugars, Carbohydrates & Glucosides;Carbohydrates & Derivatives
• Mol File: 13242-55-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 111-112 °C
• Boiling Point: 350.49°C (rough estimate)
• Flash Point: 147.3 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3270 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, DMSO, Methanol
• CAS DataBase Reference: 1,6-ANHYDRO-BETA-D-GLUCOSE-2,3,4-TRI-O-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-ANHYDRO-BETA-D-GLUCOSE-2,3,4-TRI-O-ACETATE(13242-55-2)
• EPA Substance Registry System: 1,6-ANHYDRO-BETA-D-GLUCOSE-2,3,4-TRI-O-ACETATE(13242-55-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 13242-55-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as well as for modified sugars.

InChI:InChI=1/C12H16O8/c1-5(13)17-9-8-4-16-12(20-8)11(19-7(3)15)10(9)18-6(2)14/h8-12H,4H2,1-3H3/t8-,9-,10+,11-,12-/m1/s1

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 3867-86-5 Brigl's anhydride 
• 108-24-7 acetic anhydride 
• 498-07-7 levoglucosan 
• 447-27-8 β-D-glucopyranosyl fluoride 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 121363-55-1 2,3,4-Tri-O-acetyl-6-O-p-toluenesulfonyl-D-glucopyranose 
• 87690-84-4 1,2-O-exo-cyanoethylidene-4,6-di-O-acetyl-3-O-trityl-α-D-glucopyranose 
• 108-05-4 vinyl acetate 
• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 15503-90-9 pentachlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 88526-58-3 Tri-O-nitro-1,6-anhydro-β-D-glucopyranose 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 

Downstream Products

• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 93173-23-0 1,6-anhydro-2,4-di-O-acetyl-3-O-benzoyl-β-D-glucopyranose 
• 74774-20-2 (6RS)-2,3,4,6-tetra-O-acetyl-6-phenylthio-β-D-glucopyranosyl acetate 
• 74774-11-1 (6R)-2,3,4,-tri-O-acetyl-1,6-anhydro-6-phenylthio-β-D-glucopyranose 
• 74774-15-5 (6R)-2,3,4-tri-O-acetyl-1,6-anhydro-6-methoxy-β-D-glucopyranose 
• 74774-15-5 (6S)-tri-O-acetyl-1,6-anhydro-6-methoxy-β-D-glucopyranose 
• 74774-19-9 (6S)-2,3,4,-tri-O-acetyl-1,6-anhydro-6-iodo-β-D-glucopyranose 
• 74774-14-4 (6R)-1,6-anhydro-6-phenylthio-β-D-glucopyranose 
• 74774-18-8 6-acetoxy-1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant articles and documents

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AMINE-CATALYZED TRANSFORMATION OF ENOLIC NONENZYMIC BROWNING PRODUCTS, ISOMALTOL GLYCOPYRANOSIDES INTO 1,6-ANHYDRO-β-D-HEXOPYRANOSES

The nonenzymic browning products, isomaltol D-galacto- and D-glucopyranosides, are transformed by 5:1 (v/v) triethylamine-pyrrolidine into 1,6-anhydro-β-D-galactopyranose (41percent) and 1,6-anhydro-β-D-glucopyranose (3percent), respectively.The amines, designed to simulate the amino functionality in proteins, peptides, and ammonia (eliminated by decomposition of amino acids, proteins, and peptides) relative to nonenzymic browning during the baking process, catalyzed the transformations through the production of alkoxide ions formed from deprotonation of the ring hydroxyl groups in 1 : 1 (v/v) aqueous ethanol.

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Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid

A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.

Total synthesis of the antiallergic naphtho-α-pyrone tetraglucoside, cassiaside C2, isolated from Cassia seeds

Toralactone 9-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→3)- P-D-glucopyranosyl-(1-6)-β-D-glucopyranoside (1, cassiaside C2), isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-α-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.