134680-55-0

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside
• Synonyms: methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside
• CAS NO: 134680-55-0
• Molecular Weight: 462.543
• Mol File: 134680-55-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside(134680-55-0)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside(134680-55-0)

Safety Data

• Hazardous Substances Data: 134680-55-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 181480-80-8 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 862730-60-7 tert-butyldimethyl(((2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)silane 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 134651-18-6 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-galacto-hept-6-enopyranoside 
• 1401562-80-8 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside 
• 1401562-76-2 methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside 
• 1401562-79-5 methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-L-glycero-α-D-galacto-oct-7-enopyranoside 
• 103597-18-8 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside 
• 103597-22-4 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside 
• 1207950-88-6 C₅₆H₆₀O₁₀ 
• 1254038-51-1 C₃₄H₃₅NO₅ 
• 1254038-23-7 C₃₂H₃₄O₇ 
• 128184-68-9 (1R,2S,3S,4R,5R,6S)-2,3,4-tribenzyloxy-5-<(1-methylethyl)diethylsilyl>oxy-6-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexanol 
• 134680-59-4 (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone 
• 136892-47-2 (2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone 
• 134680-57-2 (1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene 
• 134680-58-3 (3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol 

Relevant articles and documents

Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: Characterization of the reactions catalyzed by LmbR and LmbN

Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C 8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of d-erythro-d-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using d-fructose 6-phosphate or d-sedoheptulose 7-phosphate as the C3 donor and d-ribose 5-phosphate as the C5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C8 backbone of MTL.

RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material

Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers

The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.