119005-80-0

Basic information

• Product Name: B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate
• Synonyms: B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate;Beta-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate;1,6-Anhydro-2-azido-2-deoxy-beta-D-glucopyranose-3,4-diacetate
• CAS NO: 119005-80-0
• Molecular Formula: C₁₀H₁₃N₃O₆
• Molecular Weight: 271.228
• Mol File: 119005-80-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate(119005-80-0)
• EPA Substance Registry System: B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate(119005-80-0)

Safety Data

• Hazardous Substances Data: 119005-80-0(Hazardous Substances Data)

Usage

General Description

"B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate" is a chemical compound with multiple functional groups, including glucopyranose, anhydride, azide, and acetate. It is derived from glucose and is commonly used in organic chemistry and biochemistry research. B-D-Glucopyranose,1,6-anhydro-2-azido-2-deoxy-,3,4-diacetate can be used in the synthesis of various glycosidic compounds and may have potential applications in the development of new drugs or materials. Its complex structure and multiple functional groups make it an interesting target for chemical synthesis and study.

Upstream product

• 108-24-7 acetic anhydride 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 14168-65-1 mannosan 

Downstream Products

• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 

Relevant articles and documents

The oxolane ring opening of some muramic acid derivatives under acidic conditions

Synthesis of 1,6-anhydro sugars is well known in literature. The dioxolane ring exhibits at least two types of properties. It can be used as a protecting group and reaction site. This work discusses the cleavage of the 1,6-anhydro ring of muramic acid derivatives. To induce the opening of the dioxolane ring in 1,6-anhydro-D-glucose derivatives three types of reagents were used (TFA/Ac2O, Sc(OTf)3/Ac2O, H2SO4/Ac2O). This method is commonly used in sugar chemistry for opening 1,6-anhydro ring. This process led to the preparation of compounds with very good yields (80%, even 98%). In the first attempt the mixture of TFA/Ac2O (1:9) was used. Besides the main product 4, the 3,4-di-Oacetyl- 1,6-anhydro-2-azide-2-deoxy-β-D-glucopyranose was observed as a side product. Main product 4 was obtained as the mixture of α and β (2:1) anomers. Better stereoselectivity was obtained using Sc(OTf)3. In this case, the main product was received with β configuration. The best yield (65%) was obtained using a mixture of H. In this case, the main product was received with β configuration. The best yield (65%) was obtained using a mixture of H2SO4 and Ac2O and mixture of two anomers of N-acetyl-1,4,6-tri-Oacetyl- 2-deoxy-D-muramic acid ethyl ester was isolated (α and β, 1:4). Depending on which method was used to open dioxolane ring of 1,6-anhydroMur derivative we were able to control the stereochemistry of the reaction and to obtain pure α anomer or mostly β anomer.

Facile Preparation of 3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose and Some Derivatives Thereof: Useful Precursors for Oligosaccharide Synthesis

A facile, virtually one-pot synthesis of the title compound and also some of its derivatives is based on regioselective 2-substitutions of 1,6-anhydro-β-D-mannopyranose using stannylidene activation.The compounds thus prepared are useful precursors in the synthesis of glycoprotein-type oligosaccharides.