23568-35-6

Upstream product

• 100-44-7 benzyl chloride 
• 1256911-54-2 (E)-3-((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 1256911-55-3 (E,4R,5S)-6-(tert-butyldimethylsilyl)oxy-4,5-isopropylidenedioxy-1-(tetrahydropyran-2-yl)oxy-2-hexene 
• 1256911-56-4 (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenol 
• 1256911-57-5 (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenal 
• 29325-28-8 (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 
• 100-39-0 benzyl bromide 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 

Downstream Products

• 532-20-7 D-Ribose 
• 118964-42-4 5-O-Allyl-1-O-(3-O-allyl-2,5-di-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 
• 118964-41-3 1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol 
• 118964-52-6 (2R,3R,4S,5R)-4-Allyloxy-2-((2S,3R,4R)-5-allyloxy-2,3,4-tris-benzyloxy-pentyloxy)-5-benzyloxymethyl-tetrahydro-furan-3-ol 
• 118964-38-8 Acetic acid (2R,3R,4R)-4-acetoxy-2-benzyloxymethyl-5-chloro-tetrahydro-furan-3-yl ester 
• 118964-39-9 Acetic acid (3aR,5R,6R,6aR)-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 124151-37-7 Acetic acid (3R,4R,5R)-4-allyloxy-5-benzyloxymethyl-2-chloro-tetrahydro-furan-3-yl ester 
• 118964-40-2 (3aR,5R,6R,6aR)-6-Allyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 124151-36-6 5-O-benzyl-1,2,3-tri-O-acetyl-D-ribofuranoside 

Relevant academic research and scientific papers

A novel pentose synthesis via palladium(II)-catalyzed cyclization of an unstable hemiacetal

PdCl2(PhCN)2 (5 mol%)-catalyzed cyclization of a hemiacetal derived from (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H- pyran-2-yl)-4-hexenal and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n oσ*c-o) and A1,2 strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose and L-lyxose. The Japan Institute of Heterocyclic Chemistry.

SYNTHESIS OF FOUR STEREOISOMERS OF 4-AMINO-2-(HYDROXY-METHYL)TETRAHYDROFURAN-4-CARBOXYLIC ACID

The 5-benzyl ether, 15, of a 1,2,,4,5-pentanetetrol of known 2S configuration was made by a multistep synthesis from D-ribose.Ring-closure of the 1-O-otosyl derivative, 17, with retention of configuration, followed by oxidation, gave the 2S enantiomer, 22