158964-83-1

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl azide
• Synonyms: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl azide
• CAS NO: 158964-83-1
• Molecular Weight: 565.669
• Mol File: 158964-83-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl azide(158964-83-1)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl azide(158964-83-1)

Safety Data

• Hazardous Substances Data: 158964-83-1(Hazardous Substances Data)

Upstream product

• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 51250-91-0 bis(p-nitrophenyl) azidophosphonate 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose 

Downstream Products

• 150370-50-6 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose 
• 1218787-40-6 1-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-4-hydroxymethyl-1H-1,2,3-triazole 
• 1029899-23-7 (3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-benzyl-α-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 articles and documents

A Direct Br?nsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates

Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Br?nsted acid HBF4·OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron-donating and electron-withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well-tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.

"click" synthesis of nonsymmetrical bis(1,2,3-triazoles)

Chemical Fig. Repretation Unsymmetrically 1,1'-disubstituted 4,4'-bis-1 H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole Intermediates 5: (a) the stepwise Swern oxidatlon/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadiyne 9. The method is highlighted by Its compatibility with orthogonally protected and functlonallzed saccharide-peptide hybrids and its ability to be extended to the trlsubstituted counterparts 12.

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.