14440-51-8

Basic information

• Product Name: 1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-BETA-D-MANNOPYRANOSE
• Synonyms: 1,6-ANHYDRO-2,3-ISO-PROPYLIDENE-B-D-MANNOPYRANOSIDE;1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-B-D-MANNOPYRANOSE;1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-BETA-D-MANNOPYRANOSE;.beta.-D-Mannopyranose, 1,6-anhydro-2,3-O-(1-methylethylidene)-;1,6-anhydro-2,3-o-isopropylidene-β-d-mannopyranose;1,6-Anhydro-2-O,3-O-isopropylidene-β-D-mannopyranose;1,6-Anhydro-2,3-O-isopropylidene-β-D-mannopyranose ,98%;1,6-Anhydro-2,3-O-(1-Methylethylidene)-β-D-Mannopyranose
• CAS NO: 14440-51-8
• Molecular Formula: C₉H₁₄O₅
• Molecular Weight: 202.2
• Product Categories: Carbohydrates & Derivatives;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 14440-51-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 127-130 °C(lit.)
• Boiling Point: 337.275 °C at 760 mmHg
• Flash Point: 157.778 °C
• Appearance: white crystalline solid
• Density: 1.29 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly), Water (Sparingly, Hea
• PKA: 13.25±0.40(Predicted)
• CAS DataBase Reference: 1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-BETA-D-MANNOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-BETA-D-MANNOPYRANOSE(14440-51-8)
• EPA Substance Registry System: 1,6-ANHYDRO-2,3-O-ISOPROPYLIDENE-BETA-D-MANNOPYRANOSE(14440-51-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14440-51-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C9H14O5/c1-9(2)13-6-5(10)4-3-11-8(12-4)7(6)14-9/h4-8,10H,3H2,1-2H3/t4-,5-,6+,7+,8-/m1/s1

Upstream product

• 150161-01-6 2,3-O-Isopropylidene-4-O-t-butyldimethylsilyl-1,6-anhydro-β-D-mannopyranose 
• 77-76-9 2,2-dimethoxy-propane 
• 14168-65-1 mannosan 
• 67-64-1 acetone 
• 71856-30-9 dianhydroaltrose 
• 530-26-7 D-Mannose 
• 126354-67-4 2,3-isopropylidenedioxy-D-mannono-γ-lactone 
• 150160-98-8 2,3-O-Isopropylidene-6-O-(p-tolylsulfonyl)-D-mannono-1,4-lactone 
• 150160-99-9 2,3-O-Isopropylidene-5-O-tert-butyldimethylsilyl-6-O-(p-tolylsulfonyl)-D-mannono-1,4-lactone 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 6619-07-4 6-O-p-toluenesulfonyl-D-mannopyranose 
• 3458-28-4 D-Mannose 
• 7322-31-8 β-D-mannose 

Downstream Products

• 79522-93-3 4-O-(6-O-Acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2,3-O-isopropyliden-β-D-mannopyranose 
• 131940-20-0 (-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose 
• 149353-66-2 1,6-anhydro-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-2,3-O-isopropylidene-β-D-mannopyranose 
• 74808-14-3 (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 
• 74808-12-1 (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 
• 5349-02-0 1,6-Anhydro-2,3-O-isopropylidene-4-O-p-toluenesulfonyl-β-D-mannopyranose 
• 128244-18-8 1,6-anhydro-2,3-O-isopropylidene-4-O-(phenoxythiocarbonyl)-β-D-mannopyranose 
• 14168-65-1 mannosan 
• 90405-80-4 tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane 
• 14440-50-7 1,6-anhydro-2,3-O-isopropylidene-β-D-lyxo-hexopyranos-4-ulose 
• 864966-98-3 1,6-anhydro-4-O-(4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranosyl)-(1->4)-2,3-O-isopropylidene-β-D-mannopyranose 
• 887471-18-3 1,6-anhydro-4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-β-D-mannopyranose 
• 7225-53-8 (-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose 

Relevant articles and documents

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Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose

Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.

A carbohydrate synthesis employing a photochemical decarbonylation

A new route to the aldopentoses, ribose and lyxose, and the aldohexoses, talose and gulose, has been developed using chiral building blocks containing a bicyclo[3.2.1]octane framework by employing a photochemical decarbonylation reaction as the key step.