189758-76-7

Upstream product

• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 189758-74-5 (2S,3S,4R,6S)-2-Bromomethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 122204-66-4 methyl 2,6-dibromo-2,6-dideoxy-α-D-mannopyranoside 
• 69617-72-7 (3S,4S,5R,1'S)-3-bromo-5-(2'-bromo-1'-hydroxy)ethyl-4,5-dihydro-4-hydroxy-2-(3H)-furanone 

Downstream Products

• 725268-38-2 (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone 
• 189758-78-9 GS 416 
• 6272-38-4 O-benzylcatechol 
• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 

Relevant academic research and scientific papers

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.