604767-74-0

Basic information

• Product Name: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate
• Synonyms: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate
• CAS NO: 604767-74-0
• Molecular Weight: 684.764
• Mol File: 604767-74-0.mol

Chemical Properties

• CAS DataBase Reference: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate(604767-74-0)
• EPA Substance Registry System: di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate(604767-74-0)

Safety Data

• Hazardous Substances Data: 604767-74-0(Hazardous Substances Data)

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 530-26-7 D-Mannose 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 107-66-4 dibutyl phosphate 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 108-24-7 acetic anhydride 

Downstream Products

• 1092958-90-1 (2-O-benzoyl-3,4-di-O-benzyl-6-O-levuniloyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol 
• 1092959-30-2 1-O-allyl-2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,5-tri-O-benzyl-6-O-acetyl-D-myo-inositol 
• 640277-82-3 allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1→6)-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 124684-93-1 Acetic acid (2R,3S,4S,5R,6R)-2-((1S,2S,3S,4R,5S,6R)-2-allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 908853-78-1 1-O-allyl-2,6-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol 
• 175355-41-6 pent-4-enyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 161664-79-5 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Catalytic oxidation-phosphorylation of glycals: Rate acceleration and enhancement of selectivity with added nitrogen ligands in common organic solvents

(Chemical Equation Presented) The first general catalytic oxidation of glycals has been developed to afford useful glycosyl phosphates in high yield and selectivity in a domino process with the use of catalytic methyltrioxorhenium, urea hydrogen peroxide, stoichiometric dibutyl phosphate as nucleophile, and a substoichiometric amount of nitrogen ligands, such as pyridine or imidazole, in organic solvents.

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis

The emergence of multidrug-resistant tuberculosis (TB) and problems with the BCG tuberculosis vaccine to protect humans against TB have prompted investigations into alternative approaches to combat this disease by exploring novel bacterial drug targets and vaccines. Phosphatidylinositol mannosides (PIMs) are biologically important glycoconjugates and represent common essential precursors of more complex mycobacterial cell wall glycolipids including lipomannan (LM), lipoarabinomannan (LAM), and mannan capped lipoarabinomannan (ManLAM). Synthetic PIMs constitute important biochemical tools to elucidate the biosynthesis of this class of molecules, to reveal PIM interactions with host cells, and to investigate the function of PIMs as potential antigens and/or adjuvants for vaccine development. Here, we report the efficient synthesis of all PIMs including phosphatidylinositol (Pl) and phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6). Robust synthetic protocols were developed for utilizing bicyclic and tricyclic orthoesters as well as mannosyl phosphates as glycosylating agents. Each synthetic PIM was equipped with a thiol-linker for immobilization on surfaces and carrier proteins for biological and immunological studies. The synthetic PIMs were immobilized on microarray slides to elucidate differences in binding to the dendritic cell specific intercellular adhesion molecule-grabbing nonintegrin (DC-SIGN) receptor. Synthetic PIMs served as immune stimulators during immunization experiments in C57BL/6 mice when coupled to the model antigen keyholelimpet hemocyanin (KLH).

Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions

A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immuno

Methyltrioxorhenium catalyzed domino epoxidation-nucleophilic ring opening of glycals

The use of catalytic methylrhenium trioxide (MTO) and urea hydrogen peroxide in room temperature ionic liquid for the hydroxyglycosylation with glycals in a domino fashion is reported. Excellent conversions and good selectivities for the epoxidation reaction were observed. Application to the synthesis of glycosylphosphates, good glycosyl donors, has been studied.