3868-05-1

Basic information

• Product Name: 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose
• Synonyms: 1,6-Anhydro-β-D-glucopyranose 2-(4-Methylbenzenesulfonate);Levoglucosan 2-p-Toluenesulfonate;1,6-Anhydro-beta-D-glucopyranose 2-(4-methylbenzenesulfonate);1,6-Anhydro-2-O-p-toluenesulfonyl-2-D-glucopyranose
• CAS NO: 3868-05-1
• Molecular Formula: C₁₃H₁₆O₇S
• Molecular Weight: 316.328
• Product Categories: Aromatics;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 3868-05-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 117-118°C
• Boiling Point: 549.12 °C at 760 mmHg
• Flash Point: 285.898 °C
• Appearance: /
• Density: 1.557 g/cm³
• Solubility: Chloroform, Ethyl Acetate
• PKA: 12.98±0.60(Predicted)
• CAS DataBase Reference: 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose(3868-05-1)
• EPA Substance Registry System: 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose(3868-05-1)

Safety Data

• Hazardous Substances Data: 3868-05-1(Hazardous Substances Data)

Usage

Description

1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is a white solid chemical compound derived from b-D-glucopyranose, a type of sugar. It is modified with a p-toluenesulfonyl group at the 2-O position and features an anhydro ring between the 1 and 6 positions. This modification enhances its reactivity and stability in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable building block for creating complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is used as a key reactant in the syntheses of anhydro sugars. These anhydro sugars are important in the development of novel compounds with specific properties, such as improved stability or reactivity, which can be applied in various chemical and industrial processes.
Used in Research and Development:
Due to its unique structure and properties, 1,6-Anhydro-2-O-p-toluenesulfonyl-b-D-glucopyranose is also used in research and development for exploring new chemical reactions and understanding the behavior of similar compounds. This can lead to the discovery of new applications and advancements in various scientific fields.

Upstream product

• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 498-07-7 levoglucosan 
• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 16939-77-8 1,6:3,4-dianhydro-β-D-galactopyranose 
• 492-61-5 β-D-glucose 
• 1071534-24-1 O¹,O³,O⁴-triacetyl-O²,O⁶-bis-(toluene-4-sulfonyl)-β-D-glucopyranose 

Downstream Products

• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 
• 29332-85-2 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β-D-glucopyranoside 
• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 
• 4631-19-0 3,4,6-tri-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranosyl bromide 
• 4581-93-5 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-α-D-glucopyranose 
• 4627-39-8 1,3,4,6-tetra-O-acetyl-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 88142-91-0 1,6-anhydro-2-O-p-toluenesulphonyl-3,4-O-bis(trimethylsilyl)-β-D-glucopyranose 

Relevant articles and documents

PROCESS FOR THE PRODUCTION OF 1,6-ANHYDRO SUGARS

Method for synthesizing 1,6-anhydro sugars – in particular sugars that may be used as intermediates for making fondaparinux.

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.

Preparation method of fondaparinux sodium monosaccharide intermediate

The invention discloses a preparation method of a fondaparinux sodium monosaccharide intermediate. The preparation method comprises the following steps: (1) in the presence of an acid-binding agent, carrying out esterification reaction on a compound as shown in a formula (I) and a substituent sulfonic anhydride and/or a substituent sulfonyl halogen to generate a compound as shown in a formula (II); (2) carrying out a ring opening reaction on the compound as shown in the formula (II) in an acidic condition to generate a compound as shown in a formula (III); (3) carrying out benzylation reactionon the compound as shown in the formula (III) and benzyl monohalide in an alkaline condition to generate a compound as shown in a formula (IV); and (4) carrying out an azido reaction on the compoundas shown in the formula (IV) and alkali metal azide salt to generate a compound as shown in a formula (V) and caring out inner ether ring opening and acetylation reaction on the compound as shown in the formula (V) in a mixed solution of acetic anhydride and trifluoroacetic acid to generate a compound as shown in a formula (VI). The method can be used for obtaining an ideal product yield, and theraw materials are cheap, easily available and relatively few in three wastes. The formulae are as shown in the description.