138034-65-8

Upstream product

• 7757-38-2 O²,O³,O⁵,O⁶-diisopropylidene D-mannofuranose 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 591-51-5 phenyllithium 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 

Downstream Products

• 162808-23-3 (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole 
• 1417503-87-7 (1S)-1,4-di-O-allyl-1-C-phenyl-D-mannitol 
• 1417503-86-6 (1S)-1,4-di-O-allyl-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol 
• 1415308-12-1 (R)-1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol 
• 157309-48-3 (Z)-(R)-4-Acetoxy-4-[(4S,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-2-enoic acid methyl ester 
• 157309-47-2 Acetic acid (R)-[(4R,5R)-5-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methyl ester 
• 157309-46-1 Acetic acid (R)-[(4R,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 

Relevant academic research and scientific papers

Total synthesis of (-)-isoaltholactone

A short and efficient stereoselective synthesis of a styryllactone (-)-isoaltholactone has been achieved in seven steps and 33% overall yield, starting from the readily available carbohydrate D-mannose. The key steps of our synthesis involve intramolecula

Reactions of 2,3-O-isopropylidene derivatives of furanose sugars with organomagnesium and organolithium, nucleophiles

Reactions of 2,3-O-isopropylidene derivatives of furanose sugars with Grignard reagents afford stereoselectively products with an anti- (erythro-) relationship between the new chiral centre and that at C-2; the corresponding reactions with organolithium r

Stereocontrolled synthesis of four diastereomeric C-aryl manno- and talofuranosides

In a chiral-pool synthesis starting from d-mannono-1,4-lactone 1a, the four diastereomeric C-aryl furanosides (1S,4R)-4a, (1S,4S)-4b, (1R,4R)-4c, and (1R,4S)-4d were obtained in a stereocontrolled manner. The key steps of the synthetic pathway comprise a

Conformational constraints: Nature does it best with sialyl Lewis x

Selectins play a key role in the inflammatory cascade. The interaction with their physiological ligands containing the tetrasaccharide sialyl Lewis x (sLex) leads to the recruitment of leukocytes from the vascular system to the site of injury. To facilitate the interaction under the shear stress conditions present in the blood vessel, the conformation of sLex is stabilized via lipophilic inter-residual contacts. sLe x and two analogs were synthesized and evaluated for selectin binding, average conformation, and conformational dynamics. We could show that the methyl group in L-fucose is optimally suited to stabilize the sLe x core through an interaction with the β-face of D-galactose and thus enables binding to the selectins under shear stress conditions.

Goniobutenolides A and B: Serendipitous Syntheses, Relative and Absolute Configuration

The relative and absolute stereochemistries of natural goniobutenolides A and B are established as 1 and 2 respectively by short syntheses of them and their 8-epimers.