108266-98-4

Upstream product

• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 

Downstream Products

• 108182-71-4 (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose 
• 108182-67-8 methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate 
• 108182-66-7 methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranuronate 
• 748793-15-9 (2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one 
• 139534-92-2 (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one 
• 1318961-08-8 3-O-benzyl-5-(N-diphenylmethylamino)-5,6-dideoxy-1,2-O-isopropylidene-β-L-idohepto-1,4-furanose 
• 108182-68-9 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranose 
• 109145-63-3 3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose 
• 108182-70-3 (Z)-7-O-acetyl-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranose 

Relevant academic research and scientific papers

Asymmetric aza-Michael addition under ultra-high pressure: Short bias to polyhydroxylated piperidines

Two polyhydroxylated piperidines have been prepared in short sequences from diacetone gluco- and allofuranose. The key step is a piezo-aza-Michael addition of diphenylmethanamine to enoates bearing a sugar moiety in the γ-position. The combination of ultra-high pressure associated to the presence of readily available sugars chiral pool led to the expected chiral amines in good yields and excellent stereoselectivities.

Design, synthesis and antiproliferative activity of two new heteroannelated (-)-muricatacin mimics

Two new (-)-muricatacin mimics bearing a furano-furanone ring and an oxygen isostere in the side chain have been designed and synthesized and their in vitro antiproliferative activity was evaluated against several human tumour cell lines. Both analogues showed an increased activity against HL-60 cells with 17- and 185-fold higher potency than (-)-muricatacin. A straightforward synthesis of (-)-muricatacin is also disclosed.

[3+2] Cycloaddition reactions: A simple entry to the 1-aza-2-oxo-3,4,5,6- tetrahydroxybicyclo[3.3.0]octane ring system

The [3+2] intramolecular nitrone cycloaddition (INC) reaction on appropriately designed olefinic nitrones derived from D-glucose, having the nitrone at C-1 and α,β-unsaturated ester functionalities at C-5 of the sugar backbone, afforded the isoxazolidine

THE SYNTHESIS OF SOME SEVEN-CARBON SUGARS via THE OSMYLATION OF OLEFINIC SUGARS

The stereochemical outcome of the catalytic osmylation of 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-hept-6-enopyranose (10), 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose, (E)- and (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranose (20 and 27, respectively), methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate (26), (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-enofuranose, benzyl (E)- and (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (46 and 50, respectively), and methyluronate (49) has been examined.Such oxidations led to satisfactory syntheses of L-glycero-D-gluco-heptose and the corresponding heptitol (from 20), L-glycero-D-gulo-heptitol (from 26), D-glycero-D-gluco-heptitol (from 27), D-glycero-D-galacto-heptitol (from 10 and 46), (meso)-glycero-gulo-heptitol (from 49), and D-glycero-D-manno-heptitol (from 50).