16749-46-5

Basic information

• Product Name: 6-deoxy-1,2-O-(1-methylethylidene)hexofuranose
• CAS NO: 16749-46-5
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.2203
• Mol File: 16749-46-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 335.3°C at 760 mmHg
• Flash Point: 156.6°C
• Density: 1.24g/cm³
• Vapor Pressure: 8.43E-06mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 6-deoxy-1,2-O-(1-methylethylidene)hexofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-deoxy-1,2-O-(1-methylethylidene)hexofuranose(16749-46-5)
• EPA Substance Registry System: 6-deoxy-1,2-O-(1-methylethylidene)hexofuranose(16749-46-5)

Safety Data

• Hazardous Substances Data: 16749-46-5(Hazardous Substances Data)

Usage

Also Known As

6-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose

Class

Carbohydrate

Function

Protecting group for hydroxyl groups of carbohydrates

Physical Properties

White crystalline solid, sweet taste, soluble in water and polar solvents

Uses

Intermediate in synthesis of pharmaceuticals, agrochemicals, and fine chemicals

Importance

Valuable tool in organic synthesis due to unique structure and properties

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 7595-86-0 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-O⁶-(toluene-4-sulfonyl)-α-D-glucofuranose 
• 194875-04-2 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-6-iodo-6-deoxy-α-D-glucofuranose 
• 118176-19-5 3-O-acetyl-1,2-O-isoprpylidene-5,6-di-O-methanesulphonyl-α-D-glucofuranose 
• 118176-21-9 3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-mesyl-α-D-glucofuranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 75-16-1 methylmagnesium bromide 
• 32785-99-2 6-deoxy-1,2:3,5-di-O-isopropylidene-β-L-idofuranoside 
• 67-56-1 methanol 
• 19189-71-0 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-α-D-xylo-6-deoxy-hex-5-enofuranose 

Downstream Products

• 28713-37-3 3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 32785-99-2 6-deoxy-1,2:3,5-di-O-isopropylidene-β-L-idofuranoside 
• 34049-11-1 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-6-deoxy-β-L-idofuranose 

Relevant articles and documents

Improved Synthesis of 6-Deoxy-1,2-O-isopropylidene-β-L-talofuranose and 6-Deoxy-1,2-O-isopropylidene-β-L-idofuranose

The key step in the preparation of 6-deoxy-1,2-O-isopropylidene-β-L-talofuranose (7) and 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose (13) is the selective exchange of the 6-O-mesyl rest of 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-allofuranose (4) and 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-glucofuranose (10) by acetate group (potassium actate/18-crown-6).

Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose at O-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idofuranose at C-3.

Conformational analysis of cyclic phosphates derived from 5-C′ substituted 1,2-O-isopropylidene-α-D-xylofuranose derivatives

Twelve 2-phenoxy-2-oxo-1,3,2-dioxaphosphorinanes fused with a 1,2-O-isopropylidene-α-D-xylofuranose moiety in cis orientation and substituted at the C′5 position were prepared in two steps from commercially available diacetone-α-D-glucose. Their conformations, and configurations were determined by 1H and 31P NMR and X-ray crystallographic techniques. Both, chair-twisted-chair and chair-boat equilibria were observed in solution. We observed that the strong anisotropic shielding effect of the benzene ring in the phenoxy group generates an upfield shift of the H1 hydrogen atom, when the cyclic phosphates adopt a boat conformation. This is due to a relative cis-orientation of the P-phenoxy group and the H1 proton of the 1,2-O-isopropylidene-α-D-xylofuranose moiety. Therefore, the configuration of the phosphorus center (SP or RP) can be determined by 1H NMR spectroscopy. Interestingly, the crystal structure of one of the cyclic phosphates exhibits two independent molecules in the asymmetric unit, one with a chair and the other one with a boat conformation.