150370-49-3

Upstream product

• 65864-61-1 β-D-mannopyranosyl azide 
• 100-39-0 benzyl bromide 
• 65864-60-0 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-β-D-mannopyranose 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 

Downstream Products

• 150370-50-6 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose 
• 1029899-25-9 (3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one 
• 222296-27-7 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine 

Relevant academic research and scientific papers

Total synthesis of spicamycin

The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.

"Click" saccharide/β-lactam hybrids for lectin inhibition

(Figure Presented) Hybrid glycopeptide β-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "cl

Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate

The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.

Pentenyl Mannosides in the Synthesis of N-Acylmannopyranosyl Amides: Conformational Analysis of Intermediates

The reaction of a pentenyl mannopyranoside with N-bromosuccinimide in the presence of acetonitrile and a carboxylic acid leads to an N-acetyl-N-acyl-α-D-mannopyranosyl imide, the acetyl group being derived from acetonitrile, and the acyl group from the carboxylic acid.The latter can be aromatic or aliphatic as exemplified with a protected aspartic acid from which an α-mannopyranosyl asparagine is obtained.Chemoselective deacetylation can be effected either with sodium methoxide or piperidine depending on whether the other acyl group is aromatic or aliphatic, respectively. 1H NMR data, conformational and molecular mechanics analyses show that the N,N-diacyl derivatives exist in a conformation lying between a B2,5 boat and a 1S5 twist boat.