159043-21-7

Upstream product

• 31795-13-8 3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 29474-73-5 (+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate 

Downstream Products

• 159043-22-8 3-O-Benzoyl-5-O-benzyl-1,2-O-isopropyliden-6-O-(p-tolylsulfonyl)-α-D-allofuranose 
• 143504-31-8 3-O-Benzoyl-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-allofuranose 
• 159043-25-1 1,2-O-Isopropyliden-5-O-methyl-6-O-(p-tolylsulfonyl)-α-D-allofuranose 
• 159043-23-9 5-O-Benzyl-1,2-O-isopropyliden-6-O-(p-tolylsulfonyl)-α-D-allofuranose 
• 159043-29-5 5-Chlor-5-desoxy-1,2-O-isopropyliden-6-O-(p-tolylsulfonyl)-β-L-talofuranose 
• 934339-33-0 5-O-acetyl-3-O-benzoyl-6-deoxy-6-iodo-1,2-O-isopropylidene-D-allofuranose 
• 934339-35-2 3-O-benzoyl-6-deoxy-6-diethylphosphono-1,2-O-isopropylidene-D-allofuranose 
• 159043-28-4 3-O-Benzoyl-5-chlor-5-desoxy-1,2-O-isopropyliden-6-O-(p-tolylsulfonyl)-β-L-talofuranose 
• 159043-24-0 3-O-Benzoyl-1,2-O-isopropyliden-5-O-methyl-6-O-(p-tolylsulfonyl)-α-D-allofuranose 

Relevant academic research and scientific papers

Ex-chiral-pool synthesis of β-hydroxyphosphonate nucleoside analogues

A new series of mononucleotide analogues bearing a nonhydrolysable P-C bond instead of the P-O phosphate linkage is presented. We intend to set up an approach that allows the synthesis of β-hydroxyphosphonate nucleoside analogues as a single diastereoisomer. In this respect, the key "sugar-phosphonate" intermediate was obtained through an Arbusov reaction from an iodosugar derivative in which the stereochemistry of the β-hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis, Structure Elucidation and Reactions of trans-Fused 3,6-Anhydro-1,2-O-isopropylidene-α-D-hexofuranoses

Unexpectedly, the reaction of 1,2-O-isopropylidene-5,6-di-O-(p-tolylsulfonyl)-α-D-allofuranose (7) with KCN in ethanol yielded the first trans-fused 3,6-anhydro-hexofuranose 10.Besides by spectroscopic evidence the structure of 10 was proved by transformation to the tosylated acetal 13 which could also be obtained via an independent route.Further reactions of 10 all resulted in opening of the strained ring system yielding acetals (18-22).By blocking the 5-position with the alkali-resistant ether function this cyclization could also be achived by more common reagents like NaH in DMF (32). - By applying this procedure to the corresponding α-D-galactofuranose derivative 41 3,6-anhydro-α-D-galactofuranose 42 could also be obtained albeit in low yield.For comparison purposes the 3,6-anhydro-α-D-gulo derivative 47 was synthesized from easily accessible 44. - Key Words: Carbohydrates / Hexofuranoses / 3,6-Anhydro-D-hexofuranoses