117238-38-7

Upstream product

• 132880-37-6 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-2-hydroxymethyl-1-phenylsulfinyl-D-lyxo-hex-1-enitol 
• 162428-29-7 (1S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane 
• 162428-32-2 (1R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2-oxa-bicyclo[4.1.0]heptane 
• 153081-97-1 3,4,6-tri-O-benzyl-2-C-acetoxymethylgalactal 
• 74801-29-9 phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 117238-41-2 Acetic acid (2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-yl ester 

Relevant academic research and scientific papers

Synthesis of C-2 methylene O- and C-glycosides and sugar derived α-methylene-δ-valerolactones from C-2-acetoxymethyl glycals

C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H, montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)4 as catalysts. Exclusive α or β selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding α-methylene-δ-valerolactones in good yields in one step using m-CPBA in the presence of BF3·Et2O. (C) 2000 Elsevier Science Ltd.

A Facile Synthesis of Chiral α-Methylene-δ-Valerolactones

Chiral α-methylene-δ-valerolactones have been obtained from 1,2-cyclopropanated sugars in one pot by reaction with iodonium di(s-collidine)perchlorate (IDCP).

Functionally Substituted Vinyl Carbanions, 43. Convenient Transformation of Hexopyranosides into α-Methylene δ-Lactone Derivatives

Treatment of glycopyranosyl phenyl sulfoxides 2ah, l, 2bh, l with two equivalents of lithium diisopropylamide provides directly the C-2-lithiated glycal intermediates 3aAh, l, 3bAh, l which, on reaction with formaldehyde as electrophile, furnish the 2-hyd

SYNTHESIS OF METHYLENE BRIDGED C-DISACCHARIDES

Addition of glycosyl radicals to the α-methylene lactones 8 obtained from the corresponding glycopyranosyl phenylsulfoxides 5a,b in convenient two step procedures provides methylene bridged C-disaccharides in high diastereoselectivities.Thus, after reduction of the lactone moiety the methylene bridged analogs 9-11 of kojibiose, ristobiose, and α-L-fucopyranosyl(1-2)-D-galactose, respectively, were obtained.