51450-38-5

Basic information

• Product Name: 1,5-anhydro-2-deoxy-4,6-O-(1-methylethylidene)hex-1-en-3-ulose
• Synonyms: Hex-1-en-3-ulose, 1,5-anhydro-2-deoxy-4,6-O-(1-methylethylidene)-
• CAS NO: 51450-38-5
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.1892
• Mol File: 51450-38-5.mol

Chemical Properties

• Boiling Point: 264.9°C at 760 mmHg
• Flash Point: 113.2°C
• Density: 1.152g/cm³
• Vapor Pressure: 0.00943mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: 1,5-anhydro-2-deoxy-4,6-O-(1-methylethylidene)hex-1-en-3-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-2-deoxy-4,6-O-(1-methylethylidene)hex-1-en-3-ulose(51450-38-5)
• EPA Substance Registry System: 1,5-anhydro-2-deoxy-4,6-O-(1-methylethylidene)hex-1-en-3-ulose(51450-38-5)

Safety Data

• Hazardous Substances Data: 51450-38-5(Hazardous Substances Data)

Usage

Common Usage

Research and pharmaceutical applications

Role

Important intermediate in the synthesis of various organic compounds

Reactivity

Versatile

Applications

Starting material for the synthesis of complex natural products and pharmaceuticals

Structure

Unique

Value

Valuable tool in organic synthesis

Potential

Development of new drugs and materials

Upstream product

• 2873-29-2 D-glucal triacetate 
• 13265-84-4 D-glucal 
• 855270-65-4 3-O-carbamoyl-4,6-O-isopropylidene-D-glucal 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 821-09-0 n-Pent-4-enyl alcohol 
• 51450-36-3 4,6-O-isopropylidene-D-glucal 

Downstream Products

• 1187451-99-5 (Z)-(4R,5R)-1-benzylamino-5-hydroxy-4,6-O-isopropylidene-hex-1-en-3-one 

Relevant articles and documents

Protecting group and solvent control of stereo-and chemoselectivity in glucal 3-carbamate amidoglycosylation

In the Rh2(OAc)4-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups. Acyclic protection permits high α-anomer selectivi

α-N-acetylmannosamine (ManNAc) synthesis via rhodium(II)-catalyzed oxidative cyclization of glucal 3-carbamates

Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh2(OAc) 4, providing mannosamine 2-N,3-O-oxazolidinones. With iodosobenzene, incorporation of 4-penten-1-ol p

MICHAEL-type additions in the synthesis of α-O- and -S-2-deoxyglycosides

O- and S-Nucleophiles including galactose, serine and cysteine derivatives undergo MICHAEL-type additions to hex-1-en-3-uloses to furnish stereoselectivity the α-2-deoxy-ulosides. The keto function at C-3 can be reduced stereoselectively with NaBH4. Both configurations can be obtained depending on the presence or absence of CeCl3. Glycosylation takes place either base catalyzed with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or KCN/18-crown-6 or acid catalyzed by ZnI2.

AN APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE TRICHOTHECENES FROM TRI-O-ACETYL-D-GLUCAL

A chiral synthesis of the B-C ring system of trichothecenes from tri-O-acetyl-D-glucal by using a photochemical cycloaddition of acetylene to the unsaturated ketone 7, followed by acid-catalyzed rearrangement, is described.