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

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

• 68733-00-6 2,6-di-O-acetyl-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 
• 68732-99-0 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.

Dimeric structures of 1,5-anhydro-D-fructose

Upon treatment with acetic anhydride-pyridine, 1,5-anhydro-D-fructose gave the enolone 1,5-anhydro-4-deoxy-D-glycero-hex-3-eno-pyranose-2-ulose as a product of elimination, which is thus available in an overall yield of 25% from D-glucose. During this reaction, acetylated dimers of 1,5-anhydro-D- fructose were formed in a side reaction, whereas these were the only products when acidic acetylation conditions were applied. The acetylated dimers were isolated and served for an unequivocal structural assignment of dimeric forms of 1,5-anhydro-D-fructose 1 by NOESY experiments. Whereas anhydroketose 1 forms dimers in Me2SO and pyridine, its C-4 epimer, 1,5-anhydro-D-tagatose, did not form dimeric structures, neither in non aqueous nor in aqueous solvents.

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).

1,5-Anhydro-D-fructose: Stereoselective conversions to 1,5- anhydroalditols and deoxy/amino substituted analogues

1,5-Anhydro-D-fructose (1) has been converted into crystalline oximes. 1,5-Anhydroalditols and 2-amino-2-deoxy-1,5-anhydroalditols have been prepared by stereoselective reduction procedures from 1 and from the oximes, respectively.

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.