189758-87-0

Upstream product

• 16977-77-8 (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 140428-81-5 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 165331-08-8 (2R,3R,4S,5S,6R)-2-(2-Azido-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 189758-88-1 Toluene-4-sulfonic acid (2R,3R,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 

Relevant academic research and scientific papers

Development of 6-[18F]fluoro-carbohydrate-based prosthetic groups and their conjugation to peptides via click chemistry

This work describes the development of new 6-[18F]fluoro-carbohydrate-based prosthetic groups equipped with an azido arm that are able to participate in copper(I)-catalyzed cycloadditions for 18F labeling of biomolecules under mild c

Synthesis of the 2-deoxyisomaltose analogue of acarbose by an improved route to chiral valieneamines

A 2-deoxyisomaltose analogue of acarbose was stereoselectively synthesised in 11 steps with a total yield of 7% starting from 2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone (6). The latter was reduced to the lactol, converted to the methyl glycoside (7) and hydrogenated to the 6-bromo-2,6-dideoxyglycoside (8). Benzylation of the hydroxy groups, elimination of bromine to a 5-ene and Ferrier carbocyclisation gave (2S,3R)-2,3-bisbenzyloxycyclohex-5-enone (12). 1,2-addition of benzyloxymethyl lithium at -110 C gave a 6:1 mixture of tertiary alcohols 13; the (1S) isomer was the major one. Reaction with trichloroacetyl isocyanate gave a carbamate 19, which, when dehydrated to the cyanate, spontaneously underwent [1,3] sigmatropic rearrangement to an isocyanate, which on addition of methanol gave the methylcarbamate 20. Basic hydrolysis of this compound gave (2R,3R,5R)-5-amino-1-benzyloxy-methyl-2,3-bis(benzyloxy)cyclohex-6-ene (22), which could be deprotected to 2-deoxyvalieneamine (5). Reaction with 2-azidoethyl 2,3,4-tri-O-benzyl-6-O-triflyl-α-D-glucopyranoside (34) gave the secondary amine 35, which was completely de-O-protected with sodium in ammonia to give 6-deoxy-6-((1R,3R,4R)-3,4-dihydroxy-5-hydroxymethylcyclohex-5-enylamino)-D- glucose (4), the 2-deoxyisomaltose analogue of acarbose.