84207-46-5

Basic information

• Product Name: 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose
• Synonyms: 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose;1,6-Anhydro-β-D-glucopyranose 4-Diacetate 2-(4-Methylbenzenesulfonate);3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-2-D-glucopyranose
• CAS NO: 84207-46-5
• Molecular Formula: C₁₇H₂₀O₉S
• Molecular Weight: 400.4003
• Product Categories: Carbohydrates & Derivatives
• Mol File: 84207-46-5.mol

Chemical Properties

• Melting Point: 118-119°C
• Boiling Point: 525.1°C at 760 mmHg
• Flash Point: 271.4°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 4.04E-11mmHg at 25°C
• Refractive Index: 1.567
• Solubility: Ethyl Acetate, Methanol
• CAS DataBase Reference: 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose(84207-46-5)
• EPA Substance Registry System: 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose(84207-46-5)

Safety Data

• Hazardous Substances Data: 84207-46-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose is used as a synthetic intermediate for the preparation of various complex carbohydrates and their derivatives. Its unique structure allows for selective functionalization and modification, making it a valuable tool in the synthesis of bioactive compounds, pharmaceuticals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose is used as a key building block for the synthesis of glycoconjugates and glycoproteins. These biomolecules play crucial roles in various biological processes, including cell recognition, signaling, and immune response. 3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl--D-glucopyranose's ability to be selectively modified and functionalized makes it an attractive candidate for the development of novel therapeutic agents.
Used in Chemical Research:
3,4-Di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose is also used in chemical research as a model compound for studying the reactivity and selectivity of various synthetic transformations. Its unique structure provides opportunities for exploring new synthetic methodologies and developing innovative strategies for the preparation of complex carbohydrate structures.

InChI:InChI=1/C17H20O9S/c1-9-4-6-12(7-5-9)27(20,21)26-16-15(24-11(3)19)14(23-10(2)18)13-8-22-17(16)25-13/h4-7,13-17H,8H2,1-3H3

Upstream product

• 20204-83-5 O³,O⁴-isopropylidene-O²-(toluene-4-sulfonyl)-1,6-anhydro-β-D-altropyranose 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 108-24-7 acetic anhydride 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 64-19-7 acetic acid 
• 103042-48-4 3,4-di-O-acetyl-2,6-di-O-tosyl-α/β-D-glucopyranose 
• 1195588-98-7 O²-(toluene-4-sulfonyl)-1,6-anhydro-β-D-altropyranose 

Downstream Products

• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 
• 84207-50-1 3,4-di-O-acetyl-6-bromo-6-deoxy-2-O-p-toluenesulfonyl-α-D-glucopyranosyl bromide 
• 4631-19-0 3,4,6-tri-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranosyl bromide 
• 3868-05-1 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose 
• 4627-39-8 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 4581-93-5 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranose 

Relevant articles and documents

A practical large-scale access to 1,6-anhydro-β-D-hexopyranoses by a solid-supported solvent-free microwave-assisted procedure

Microwave irradiation of 6-O-tosyl or 2,6-di-O-tosyl peracetylated hexopyranoses absorbed on basic alumina in a dry medium afforded the corresponding 1,6-anhydro-β-D-hexopyranoses. A direct access to 1,6:3,4-dianhydro-β-D-altropyranose (16) from D-glucose is also described.

PREPARATION OF 1,6:3,4-DIANHYDRO-β-D-ALTROPYRANOSE AS STARTING SUBSTANCE FOR THE SYNTHESIS OF 3-SUBSTITUTED D-MANNOSE DERIVATIVES

Acetolysis of 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-galactopyranose (I) gave 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose (II) which was converted with sodium methoxide to 1,6:3,4-dianhydro-β-D-altropyranose (X).The 1,6-anhydride bond in diacetate II was cleaved with acetic anhydride or hydrogen bromide in acetic acid under formation of a mixture of anomeric tetraacetates of 2-O-p-toluenesulfonyl-D-glucopyranose or the corresponding acetates of α-D-glucopyranosyl bromide XIII and its 6-bromo-6-deoxy derivative XIV.