37776-17-3

Basic information

• Product Name: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose
• Synonyms: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose
• CAS NO: 37776-17-3
• Molecular Weight: 292.332
• Mol File: 37776-17-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose(37776-17-3)
• EPA Substance Registry System: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose(37776-17-3)

Safety Data

• Hazardous Substances Data: 37776-17-3(Hazardous Substances Data)

Upstream product

• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 100-44-7 benzyl chloride 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 37776-15-1 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 64656-76-4 Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose 
• 18006-25-2 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 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 
• 19877-13-5 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 

Downstream Products

• 149302-62-5 1,2-O-isopropylidene-3-O-methyl-6-O-benzyl-β-L-idofuranose 
• 149302-63-6 1,2-O-isopropylidene-3-O-methyl-5-deoxy-5-azido-6-O-benzyl-α-D-glucofuranose 
• 42926-91-0 3-O-benzyl-1,6-anhydro-β-L-idopyranose 
• 209849-12-7 (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol 
• 334834-19-4 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside 
• 657395-01-2 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 657395-02-3 6-O-acetyl-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 
• 657395-07-8 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate 
• 657395-06-7 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl levulinate 
• 1439518-81-6 C₂₅H₂₆O₅S 
• 1439516-36-5 C₂₅H₂₉BrO₅S 
• 1439516-28-5 C₂₅H₂₇BrO₅S 
• 1439519-61-5 C₂₅H₂₈O₅S 
• 1439516-03-6 C₂₂H₂₅BrO₅S 

Relevant articles and documents

Synthesis and Glycosylation Properties of C6-Silylated Ido- and Gluco-Pyranosyl Donors

Silyl groups are widely used as alcohol protecting groups and their study has provided insight on some very remarkable structure and reactivity features within carbohydrate chemistry. However, not much work has been put into the effect on the reactivity of silyl groups directly attached to the sugar carbon chain. In this work, we have developed a synthetic methodology to obtain both d-glucosyl and l-idosyl donors containing a dimethylphenylsilyl group directly attached to C6. Glycosylation and competition experiments with different glycosyl acceptors have shown that this group is completely stable under glycosylation conditions and enhances reactivity beyond what a benzyl group attached to the sugar oxygen would do. Finally, we found adequate conditions for the protodesilylation of Si-containing glycosides to yield the 6-deoxy sugar analog.

METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE- -L-FURAN IDOSE

Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is

Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin

A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.