211800-60-1

Basic information

• Product Name: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose
• Synonyms: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose
• CAS NO: 211800-60-1
• Molecular Weight: 228.202
• Mol File: 211800-60-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose(211800-60-1)
• EPA Substance Registry System: 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose(211800-60-1)

Safety Data

• Hazardous Substances Data: 211800-60-1(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 75414-43-6 1,5-D-anhydrofructose 

Downstream Products

• 68732-99-0 1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose 
• 406461-53-8 1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulose 
• 68733-00-6 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose 

Relevant articles and documents

Synthesis and co-polymerization of an unsaturated 1,5-anhydro-D-fructose derivative

An unsaturated derivative, 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero- hex-3-enopyranos-2-ulose (3), was obtained via regioselective elimination and acetylation of monohydrated 1,5-anhydro-D-fructose (1) in a single step reaction. High yield (80%) was achieved without any dimeric by-products. Its co-polymerization to saccharide polymers was investigated with different commercial vinyl co-monomers. Co-polymers were obtained and characterized.

A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-d-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-d-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

Structure of 1,5-anhydro-D-fructose: X-ray analysis of crystalline acetylated dimeric forms

Acetylation of 1,5-anhydro-D-fructose under acidic conditions gave two crystalline acetylated dimeric forms, which by X-ray analysis were shown to be diastereomeric spiroketals formed between C-2 and C-2/C-3. The structures of the compounds differed only at the configuration at C-2. Acetylation or benzoylation of 1,5-anhydro-D-fructose in pyridine yielded 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enos-2-ulopyra-nose or crystalline 1,5-anhydro-3,6-di-O-benzoyl-4-deoxy-D-glycero-hex-3-enos-2-ulo-pyranose.