850223-35-7

Upstream product

• 130259-14-2 (2S,3R,4E)-2-azido-3-O-benzylsphingosine 
• 850223-34-6 (E)-(2R,3R)-3-Benzyloxy-octadec-4-ene-1,2-diol 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 201139-13-1 Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester 
• 201139-02-8 Octadecanoic acid ((E)-(1S,2R)-2-benzyloxy-1-hydroxymethyl-heptadec-3-enyl)-amide 

Relevant academic research and scientific papers

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.

'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

A stereocontrolled synthesis of globotriaosylceramide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting 'armed-disarmed' glycosidation methodology based on glycosyl donors and acceptors carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl(1→4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient.