76801-66-6

Upstream product

• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 19877-13-5 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 94844-71-0 1,2-O-Isopropyliden-6-O-methyl-5-desoxy-α-D-xylohexofuran-5-enose 
• 53167-11-6 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 57575-19-6 2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol 
• 34370-91-7 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 308290-81-5 C₁₅H₁₈O₅ 

Downstream Products

• 124771-29-5 (2R,3S)-2-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propionaldehyde 
• 124771-29-5 (2S,3R)-2-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propionaldehyde 
• 609355-96-6 Benzyl-[2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-amine 
• 1373283-23-8 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 
• 1373283-21-6 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 
• 114244-55-2 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-methyl-β-L-idofuranose 
• 124794-65-6 Acetic acid (2R,3S,4R,5S)-2-acetoxy-3-benzyloxy-5-[(R)-benzyloxy-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methyl]-tetrahydro-pyran-4-yl ester 
• 124794-65-6 Acetic acid (2S,3S,4R,5S)-2-acetoxy-3-benzyloxy-5-[(R)-benzyloxy-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methyl]-tetrahydro-pyran-4-yl ester 
• 124771-31-9 (3aR,5R,6S,6aR)-6-Benzyloxy-5-[(4R,5R)-2,2-dimethyl-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxan-5-yl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 124771-31-9 (3aR,5R,6S,6aR)-6-Benzyloxy-5-[(4S,5S)-2,2-dimethyl-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxan-5-yl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 609355-97-7 5,6-dideoxy-6-(N-benzyloxycarbonyl)amino-1,2-O-isopropylidene-α-D-gluco-furanose 
• 609355-98-8 (2S,3S,4R)-trihydroxyazepane 

Relevant academic research and scientific papers

General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

Synthesis of a furanosyl-pyranone derivative related to the tri-o-heterocyclic core of herbicidins

A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels-Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.

Pd(0)/C catalyzed efficient Wacker oxidation of functionalized terminal olefins

Wacker oxidation of terminal olefins was carried out at room temperature and atmospheric pressure by using Pd(0)/C in THF/H2O (9:1). Palladium(0)/C was proven to be highly efficient catalyst for the Wacker oxidation of terminal olefins to the corresponding methyl ketones. The catalyst was reusable while maintaining its activity and selectivity to a high degree.

An expeditious synthesis of a (3S,4S,5R)-trihydroxyazepane

A practical approach for the synthesis of the (2S,3S,4R)-trihydroxyazepane 1d has been reported. Starting from α-D-xylo-pentodialdose, readily available from D-glucose, the sequence involves Wittig olefination and reductive amination as key steps.

SYNTHESIS OF A HIGHER CARBON SUGAR VIA DIRECTED ALDOL CONDENSATION

3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexadialdo-1,4-furanose (2) upon treatment with LiN(TMS)2 at -50 deg C furnished the enolate which reacted with methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside-6-ulose (5) to afford two erythro aldols 3 and 4