158535-90-1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 158570-84-4 2,3,4,6-tetra-O-benzyl-D-galactitol 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 100-44-7 benzyl chloride 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 

Downstream Products

• 774599-32-5 (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one 
• 931397-80-7 2,3,4,5,6-penta-O-benzyl-1-O-tert-butyldimethylsilyl-D-galactitol 
• 931397-84-1 2,3,4,5,6-penta-O-benzyl-D-galactitol 
• 931397-87-4 phosphoric acid dibenzyl ester 2,3,4,5,6-pentakis-benzyloxy-hexyl ester 
• 774599-20-1 (4S,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-cyclohex-2-enone 
• 774599-18-7 (Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal 
• 774599-19-8 (1R,4S,5S,6S)-4,5,6-tribenzyloxy-3-((benzyloxy)methyl)-cyclohex-2-enol 
• 774599-33-6 (Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol 
• 774599-17-6 tert-Butyl-dimethyl-((Z)-(2S,3S,4S)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enyloxy)-silane 
• 131379-12-9 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-O-(methoxymethyl)-L-galactitol 

Relevant academic research and scientific papers

Synthesis and analysis of substrate analogues for UDP-galactopyranose mutase: Implication for an oxocarbenium ion intermediate in the catalytic mechanism

(Chemical Equation Presented) UDP-D-galactofuranose (2), which is essential for both cell growth and virulence in many pathogenic microorganisms, is converted from UDP-D-galactopyranose (UDP-Galp, 1) by the flavin adenine dinucleotide (FAD)-dependent enzyme UDP-galactopyranose mutase (UGM). Here, we report the synthesis of UDP-GalOH (13) and show it as an inhibitor for UGM with a binding affinity similar to that of 1. These results are more consistent with a mechanism involving an oxocarbenium ion intermediate in UGM catalysis.

Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes

Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.