10163-09-4

Basic information

• Product Name: 5-[(acetyloxy)methyl]-2-oxohexahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate
• CAS NO: 10163-09-4
• Molecular Formula: C₁₃H₁₇NO₉
• Molecular Weight: 331.2754
• Mol File: 10163-09-4.mol

Chemical Properties

• Boiling Point: 522.5°C at 760 mmHg
• Flash Point: 269.8°C
• Density: 1.4g/cm³
• Vapor Pressure: 5.17E-11mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: 5-[(acetyloxy)methyl]-2-oxohexahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(acetyloxy)methyl]-2-oxohexahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate(10163-09-4)
• EPA Substance Registry System: 5-[(acetyloxy)methyl]-2-oxohexahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate(10163-09-4)

Safety Data

• Hazardous Substances Data: 10163-09-4(Hazardous Substances Data)

Upstream product

• 5432-46-2 acetyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside hydrochloride 
• 5348-99-2 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside 
• 75-08-1 ethanethiol 
• 463-71-8 thiophosgene 
• 7388-99-0 β-D-mannopyranosyl amine 
• 108-24-7 acetic anhydride 
• 17460-45-6 tetra-acetyl glucosamine 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 
• 130259-34-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-nitrobenzyloxycarbonylamino)-β-D-glucopyranose 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 7597-81-1 (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate 
• 70866-07-8 N₁-(2-chloroethyl)-N₃-glucosamino-N₁-nitrosourea 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranose 
• 14131-62-5 D-glucosamine hydrochloride 

Relevant articles and documents

cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines

1,2-cis-Fused bicyclic sugar thiocarbamates of gluco and manno configurations have been prepared by treatment of the corresponding O-unprotected amino sugars and glycopyranosyl amines with thiophosgene. The reactivity of these compounds towards amines has been studied in order to determine whether these compounds could act as latent isothiocyanates; it is shown that 1,2-cis-fused bicyclic sugar thiocarbamates are more stable than their trans analogues, and are not transformed into thioureas upon treatment with amines. An unprecedented isomerization of a peracetylated glucopyranoso[2,1-d]oxazolidine-2-thione into a glucopyranoso[2,1-d]thiazolidin-2-one in DMF is also reported. The structure of this thiazolidin-2-one was confirmed by X-ray crystallography.

Systematic Structural Characterization of Chitooligosaccharides Enabled by Automated Glycan Assembly

Chitin, a polymer composed of β(1–4)-linked N-acetyl-glucosamine monomers, and its partially deacetylated analogue chitosan, are abundant biopolymers with outstanding mechanical as well as elastic properties. Their degradation products, chitooligosacchari

New synthesis of glycolipid immunostimulants RC-529 and CRX-524

An efficient and scalable synthesis of the potent vaccine adjuvant RC-529 (3) and TLR4 agonist CRX-524 (4) is described in eight steps from 1,3,4,6-tetra-O-acetyl-2-amino-2-benzyloxycarbonyl-2-deoxy-β-d- glucopyranose (10c) in ca. 25% overall yield. The synthesis features the strategic use of the N-Cbz group for β-glycosylation and the selective N,N,O-triacylation of common advanced intermediate 15 with (R)-3- tetradecanoyloxy or decanoyloxytetradecanoic acid (8, 9) late in the synthesis. A new method for preparing and enhancing the enantiopurity of (R)-3-hydroxytetradecanoic acid (6), a key component of 3 and 4 as well as bacterial lipid A, is also described.

Synthesis of sugar isocyanates and their application to the formation of ureido-linked disaccharides

The present work describes a facile and practical route to carbohydrate-based isocyanates, a reactive and appealing family of chiral heterocumulenes, wich can be easily converted into disaccharides and pseudodisaccharides interconnected by urea moieties.

The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions

1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-D-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-α-D-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity.An oxazolidone was formed as the main product from the reaction of some of the glucopyranosylbromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.

N-Allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glucosylation in Koenigs-Knorr reactions and in Lewis acid catalysed condensations

The use of suitably blocked D-glucosamine derivatives possessing the N-allyloxyxarbonyl protective group of the amino function represents potential new routes to 1,2-trans-glucosylations.Both 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glu

The N-allyloxycarbonyl derivative of D-glucosamine: a potent precursor of β-glycosidation.

The allyloxycarbonyl protective group of the amino function is a potent precursor of β-D-glucosidation of D-glucosamine and can be selectively removed or preserved in the presence of other usual carbohydrate protective groups.