41341-73-5

Basic information

• Product Name: (E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose
• Synonyms: (E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose
• CAS NO: 41341-73-5
• Molecular Weight: 276.332
• Mol File: 41341-73-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose(41341-73-5)
• EPA Substance Registry System: (E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose(41341-73-5)

Safety Data

• Hazardous Substances Data: 41341-73-5(Hazardous Substances Data)

Upstream product

• 18439-45-7 3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose 
• 917-64-6 methyl magnesium iodide 
• 115431-21-5 C₂₂H₂₆N₂O₆S 
• 78784-97-1 5-Brom-5,6-didesoxy-1,2-O-isopropyliden-β-L-ido-hexofuranose 
• 17668-66-5 6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 23313-03-3 (R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate 
• 120368-01-6 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose 
• 505-23-7 1,3 dithiane 
• 41341-69-9 3-O-Benzyl-5-brom-5,6-didesoxy-1,2-O-isopropyliden-β-L-ido-hexofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 

Downstream Products

• 120575-52-2 C₁₈H₂₂O₅ 
• 120575-51-1 C₁₈H₂₀Cl₂O₅ 

Relevant articles and documents

Caveat in alkylative fragmentation of aldehyde tosylhydrazones of cyclic ethers

Tosylhydrazones of aldehydes at the α-position of cyclic ethers when exposed to carbon nucleophiles produce either ring opened alkylated olefinic alcohols and/or cyclic alkylated vinyl ethers, the ratio of which is dependent on nature of hydrazone and nucleophile used.

Fluorination Reactions at C-5 of 3-O-Benzyl-6-deoxy-1,2-isopropylidenehexofuranoses

Fluorination reactions of 2-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-, β-L-ido-, α-D-allo-, and β-L-talo-furanoses (1, 2, 3, and 4) were investigated.The reaction of 1 with diethylaminosulfur trifluoride (DAST) predominantly produced 2-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose with the retention of the configuration at C-5.Both of the fluorides with retained and inverted configurations were obtained in the fluorination of 2 with DAST.In contrast, only the inversion of the configuration occurred when 3 and 4 were reacted with DAST.The reactions of the methanesulfonates of 3 and 4 with tetrabutylammonium fluoride (TBAF) and those of their trifluoromethanesulfonates with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) gave the 5-deoxy-5-fluoro derivatives with the inversion of each configuration and the 5,6-unsaturated derivative.However, the reactions of the sulfonates of 1 and 2 overwhelmingly produced the 4,5- and 5,6-eliminated derivatives.For the reaction in which the steric hindrance of the benzyloxyl group at C-3 and the electronic repulsion of ring oxygen to the SN2 displacement with fluoride anion are significant, such as the fluorination of 1 with DAST, the SNi mechanism is reasonable.

Chiral Building Units from Carbohydrates, XI. - 2-Lithio-1,3-dithiane-induced Reactions of 5,6-Dideoxy-5-iodohexofuranoses Leading to Open-chained Heptose Trimethylene Dithioacetals

The reaction of 5,6-dideoxy-5-iodohexofuranoses 5b, 7c, 8, 8a, and 20 with a large excess of 2-lithio-1,3-dithiane (1) yields the open-chained heptose trimethylene dithioacetals 21, 23, 24, 25, and 26.L-Configurated 5-iodides give Z-olefines, D-configurat