246864-29-9

Upstream product

• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 441044-67-3 (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine 
• 246864-26-6 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol 
• 441044-66-2 (S)-S-acetyl-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine 
• 246864-27-7 (S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine 
• 89064-71-1 β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 246864-28-8 (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(sulfonylmethyl)-1,3-oxazolidine 

Downstream Products

• 441044-68-4 5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol 
• 246864-34-6 methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate 
• 1069116-82-0 [(R)-1-Hydroxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

exo-Glycal approaches to C-linked glycosyl amino acid synthesis

Two novel routes to C-linked glycosyl amino acids are described; the first involves elaboration of an exo-glycal and subsequent Ramberg-Backlund rearrangement of a sulfone intermediate to give, after functional group manipulation, a protected C-glycosyl serine, while the second uses hydroboration-Suzuki coupling of the same exo-glycal to produce ultimately the corresponding C-glycosyl asparagine analogue.