6386-26-1

Upstream product

• 100-44-7 benzyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 14362-29-9 α-D-glucurono-γ-lactone 
• 5111-13-7 (1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 

Downstream Products

• 5123-94-4 5-Benzyl-D-glucofuranose 
• 26922-94-1 (1S,3R,4R,5S,8R)-8-benzyloxy-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 
• 1394245-86-3 C₂₄H₄₀O₇Si 
• 1394245-99-8 (5S)-epi-vittarilide A 
• 1394245-94-3 C₃₉H₇₂O₉Si₄ 
• 1394245-92-1 C₂₀H₂₂O₆ 
• 1394245-97-6 C₂₅H₃₂O₇ 
• 864512-90-3 trans-caffeoyl-6-O-D-glucono-γ-lactone 
• 1394245-90-9 C₃₉H₇₂O₉Si₄ 
• 142719-12-8 C₂₂H₃₆O₆Si 
• 5123-95-5 5-Benzyl-D-glucose-phenylosazon 
• 849624-16-4 (1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane 
• 849624-15-3 (1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane 
• 849624-14-2 (1R,4R,5R,8R)-8-benzyloxy-3-methoxy-4-hydroxy-2,6-dioxabicyclo[3.3.0]octane 

Relevant academic research and scientific papers

First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata

The first stereocontrolled synthesis of vittarilide-A and its C5-epimer was completed from d-glucuronolactone. Comparison with the spectroscopic properties reported for authentic material has given a clear indication as to the absolute stereochemistry of the natural vittarilide-A.

Stereodivergent synthesis of new amino sugars, furanodictines A and B, starting from d-glucuronolactone

An efficient and divergent strategy for the total synthesis of the first 3,6-dihydroaminosugars, furanodictines A (2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-glucofuranose) and B (2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-mannofuranose), has been developed. The synthetic process is featured by readily accessible and stereodefined manipulation of highly functionalized bicyclic tetrahydrofuran derivatives incorporating the glucuronolactone (common starting material)-derived skeleton.

An efficient and straightforward synthetic process to an amino sugar analogue, furanodictine B

A convenient and practical strategy for the construction of a natural amino sugar analogue, furanodictine B, isolated from the multicellular fruit body has been developed in an optically active form. The synthetic process is based on readily accessible and stereodefmed manipulation of the highly functionalized bicyclic derivative incorporating the glucuronolactone-derived skeleton.

Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondary vic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), ca. 2:1 (b), and ca. 1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d).A qualitatively similar result is observed upon O-alkylation of diols (1a-e) with 2-methoxyethanol tosylate.