718613-98-0

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 114817-96-8 (4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane 
• 213767-09-0 2,3-O-isopropylidene-L-erythrofuranose 

Downstream Products

• 718613-99-1 (3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester 
• 1392007-29-2 (3R,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine 
• 1392007-32-7 (3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine 
• 1392007-54-3 (4aR,6S,7R,7aR)-1-benzyl-7-acetoxy-6-acetoxymethyl-4a-methoxy-hexahydro-1H-furano[3,2-c][1,2]oxazine 
• 1392007-53-2 (4aR,6S,7R,7aR)-1-benzyl-7-hydroxy-6-hydroxymethyl-4a-methoxy-hexahydro-1H-furano[3,2-c][1,2]oxazine 
• 1392007-46-3 (2R,3R,4R,4'R,5'S)-4-benzylamino-4-(5'-hydroxymethyl-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-methoxybutan-1,2-diol 
• 1392007-36-1 (3S,4S,5S,4'R,5'S)-2-benzyl-3-[5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-3,4,5,6-tetrahydro-2H-[1,2]oxazine-5-ol 
• 718614-00-7 Acetic acid (3R,4S,5S)-2-benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-ylmethyl ester 
• 718614-05-2 [(3R,4S,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-yl]-methanol 
• 718614-01-8 Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis of a branched chain aza-C-disaccharide via the cycloaddition of a chiral nitrone to an alkene, both sugar derivatives

A multistep synthesis of a protected aza-C-disaccharide derivative with a pyrrolidine ring as the azasugar component is described. The key step is a stereoselective cycloaddition reaction of a chiral nitrone derived from D-ribose and a sugar alkene derived from D-galactose. An intramolecular N-alkylation followed by a reductive cleavage of the isoxazolidine N-O bond, in one pot, gave the final product.

Application of L-erythrose-derived nitrones in the synthesis of polyhydroxylated compounds via 3,6-dihydro-2H-1,2-oxazine derivatives

Enantiopure 3,6-dihydro-2H-1,2-oxazines were prepared by [3+3] cyclisations starting from lithiated methoxyallene and the L-erythrose-derived nitrones 1' and 3. The role of the side-chain protective group, which steers the highly selective formation of either anti- or syn-configured products, was demonstrated. A hydroboration/oxidation protocol smoothly converted 1,2-oxazine derivative syn-5 into secondary alcohol 6. After deprotection, polyhydroxylated tetrahydro-2H-1,2-oxazine 11, which can be regarded as an azasugar, was isolated. Analogous treatment of 1,2-oxazine anti-5 with the borane not only provided the expected secondary alcohol 7, but it also induced reduction of the C=C bond and ring opening. Treatment of syn-5 and anti-2 with hydrochloric acid in methanol induced deprotections and cyclisations leading to bicyclic tetrahydro-2H-1,2-oxazine derivatives. The second ring can be either a furan or a pyran ring. In the syn series, furan derivative 12 was formed exclusively, and its hydrogenolysis led to enantiopure aminofuran derivative 14. Acid-promoted rearrangement of unprotected anti-2 led to a mixture of bicyclic compounds with furan or pyran rings fused to the 1,2-oxazine core. However, when TBDPS-protected compound 20 was used it cleanly led to 1,2-oxazine 21 with a fused furan ring and then to aminofuran 22. Alternatively, the N-O bond in unprotected anti-2 was chemoselectively reduced with samarium diiodide, efficiently generating highly functionalized allylic alcohol 23. Acid-promoted cyclisation and deprotection furnished furan derivative 24. Mechanistic suggestions to explain the different outcomes of the acid-induced transformations are provided. Overall, it is demonstrated that the stereodivergent addition of lithiated alkoxyallenes to L-erythrose-derived nitrones allow flexible access to a series of enantiopure amino polyols, including aminofuran derivatives. Copyright