26922-94-1

Upstream product

• 100-39-0 benzyl bromide 
• 27821-03-0 3,6-Anhydro-1,2-O-isopropyliden-α-D-glucofuranose 
• 14362-29-9 α-D-glucurono-γ-lactone 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 94933-92-3 3-O-Acetyl-1,2-O-isopropyliden-D-glucofuranose-5,6-sulfit 
• 5111-13-7 (1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 
• 6386-26-1 O¹,O²-isopropylidene-O⁵-benzyl-α-D-glucofuranose 

Downstream Products

• 259746-16-2 1,2-di-O-acetyl-3,6-anhydro-5-O-benzyl-α,β-D-glucofuranose 
• 628292-86-4 Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester 
• 849624-17-5 (1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-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 
• 849624-16-4 (1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane 
• 1394922-37-2 C₂₆H₂₈O₈ 
• 72631-67-5 (1R,4S,5R,8R)-8-benzyloxy-2,6-dioxabicyclo<3.3.0>octan-4-ol 
• 259746-17-3 6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine 
• 259746-18-4 9-(5'-O-benzyl-3',6'-anhydro-β-D-glucofuranosyl)-inosine 
• 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

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.

First example of 5/6-O-linked pseudosaccharides: synthesis of bicyclic nucleosides containing azido or extended carbohydrate moiety

Treatment of the d-glucose-derived substrate 1 with sodium hydride in tetrahydrofuran provided 3,6-anhydro monosaccharide 2, along with the 5,6-ether linked pseudodisaccharide 3, and pseudotrisaccharide 4. However, reaction of 1 with sodium ethoxide in ethanol afforded 2 as the sole product, elaborated to the bicyclic azidonucleosides 9 and 16. Acetylated bicyclic nucleosides 17-19 with extended carbohydrate residues have been synthesized from 3.

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.

Synthesis of 3,6-anhydro sugars from cyclic sulfites and sulfates and their applications in the preparation of bicyclonucleoside analogues of ddC and ddA

Cyclic sulfates 21-23 and sulfite 27 derived from glucofuranose lead to the 3,6-anhydrosugar 28 in excellent yields when treated with sodium sulfite or in basic media. When treated with sodium sulfite, the 3-deoxy derivative 24 fails to give the intramolecular cyclization which leads to the anhydrosugars. Instead it gives the disulfonate derivative 26. 28 was used as starting material to prepare bicyclonucleosides 43 and 46, which are analogues of the anti-HIV agents ddC and ddA.