130259-14-2

Basic information

• Product Name: (2S,3R,4E)-2-azido-3-O-benzylsphingosine
• Synonyms: (2S,3R,4E)-2-azido-3-O-benzylsphingosine
• CAS NO: 130259-14-2
• Molecular Weight: 415.619
• Mol File: 130259-14-2.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-azido-3-O-benzylsphingosine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-azido-3-O-benzylsphingosine(130259-14-2)
• EPA Substance Registry System: (2S,3R,4E)-2-azido-3-O-benzylsphingosine(130259-14-2)

Safety Data

• Hazardous Substances Data: 130259-14-2(Hazardous Substances Data)

Upstream product

• 103348-49-8 2-azido-sphingosine 
• 850223-34-6 (E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol 
• 162019-93-4 (2S,3R,4E)-2-azido-3-benzyloxy-1-trityloxy-4-octadecene 

Downstream Products

• 1393355-25-3 2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-azido-3-O-benzyl-4-octadecene-1,3-diol 
• 1393355-24-2 2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-azido-3-O-benzyl-4-octadecene-1,3-diol 
• 850223-35-7 (E)-(2S,3R)-2-Amino-3-benzyloxy-octadec-4-en-1-ol 
• 162019-94-5 (2S,3R,4E)-3-benzyloxy-1,2-(p-tolylsulfonylimino)-4-octadecene 
• 1597422-10-0 (2S,3R,4E)-2-azido-1-(4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyloxy)-3-benzyloxyoctadec-4-ene 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 

Relevant articles and documents

Fluorine-directed β-galactosylation: Chemical glycosylation development by molecular editing

Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1). Copyright

Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release a broad range of bioactive cytokines. In an effort to understand the structure-activity relationships, we have carried out synth

Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue

The title compounds (1, 2) were synthesized from (2R,3S)-2-O-benzyl-3,4-O- (3′-pentylidene)-2,3,4-trihydroxybutanal (5). Installation of the E-double bond and aliphatic chain into the sphingosine base was effected by a sequence of Horner-Wadsworth-Emmons olefination of 5, conversion to allylic acetate 8, and copper-mediated Grignard coupling. The method is versatile, allowing a broad variety of aliphatic chains to be introduced in the organocuprate coupling step.

Synthesis of 5a-Carba-&β-D-glycosylceramide Analogs Linked by Imino, Ether and Sulfide Bridges

Carbocyclic analogs of glycoceramides, (2S,3R,4E)-1-(5a-carba-β-D-glycopyranosyl)-2-(hexadecanoylamino)-4-octadecen-3-ols E-3 - E-6, linked by imino, ether and sulfide bridges, were synthesized by coupling of aziridines, as the sphingosine precursors, wit