136945-16-9

Upstream product

• 136945-15-8 allyl O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 67124-60-1 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide 
• 136945-14-7 O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate 
• 136945-13-6 [(2R,3S,4R,5R)-3,4-diacetoxy-6-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl acetate 
• 97576-68-6 (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol 
• 187455-96-5 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-ethylsulfanyl-tetrahydro-pyran-4-yl ester 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 144923-59-1 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 59042-16-9 (3R,4R,5S,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 871116-05-1 1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside 
• 871115-97-8 O-(3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-D-glucopyranosyl) trichloroacetimidate 
• 871115-95-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside 

Downstream Products

• 136945-17-0 O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-1-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranose 
• 136945-18-1 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid 

Relevant academic research and scientific papers

New diacylamino protecting groups for glucosamine

Glucosamine was 'transformed into N-diphenylmaleoyl (DPM), N-(3,3-dimethylglutaryl) (DMG), and N-diglycolyl (DG) derivatives which furnished O-acetyl-protected O-glycosyl trichloroacetimidates 3, 12, and 20, respectively, as glycosyl donors. Their reactio

N-Trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors

D-Glucosamine can be readily transformed into 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichlorothoxycarbonylamino)-D -glucopyranose (2). From this intermediate valuable glycosyl donors can be obtained; reaction with ethanethiol in the presence of boron trifluoride etherate afforded ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)β-D -glucopyranoside 4) which gave, upon N-acetylation, the N-acetyl-N-trichloroethoxycarbonyl derivative (5). Selective removal of the 1-O-acetyl group in 2 followed by treatment with trichloroacetonitrile in the presence of base afforded 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-tricchloroethoxycarbonylamino)-α-D -glucopyranosyl trichloroacetimidate (6). Reaction of 5 with five selectively protected glycosides as glycosyl accepters in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid as the promoter system furnished the corresponding β-glycosides in good yields, thus exhibiting the valuable glycosyl donor properties of 5. Reductive removal of the trichloroethoxycarbonyl (Teoc) group afforded the corresponding N-acetyl-protected saccharides in high yields. The imidate 6 reacted with three of the above accepters in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate to give the β-linked disaccharides in even better yields. The direct replacement of the N-Teoc group by the N-acetyl group using zinc/acetic anhydride, via the free amines as transient intermediates, adds to the high efficiency and convenience of this methodology.

The synthesis of partial structures of complex N-glycoproteins

Comparable syntheses of β-D-GlcpNAc-(1→2)-[β-D-GlcpNAc-(1→6)]-α-D-Manp-(1→6)-β-D-ManpO (CH2)8CO2Me and β-D-GlcpNAc-(1→2)-α-D-Manp-(1→3)-β-D-ManpO(CH2)8CO2Me with the glycosyl halide and imi