102208-55-9

Basic information

• Product Name: 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol
• Synonyms: 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol
• CAS NO: 102208-55-9
• Molecular Weight: 434.532
• Mol File: 102208-55-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol(102208-55-9)
• EPA Substance Registry System: 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol(102208-55-9)

Safety Data

• Hazardous Substances Data: 102208-55-9(Hazardous Substances Data)

Upstream product

• 102208-53-7 (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 
• 122194-14-3 2-deoxy-2-selenophenyl-3,4,6-tri-O-benzyl-α-glucopyranose 
• 129116-33-2 3,4,6-tri-O-benzyl-2,5-anhydro-D-mannose dimethylacetal 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 94283-95-1 (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 287733-97-5 (2S,3R,4R,5R)-1,3,4,5-Tetrakis-benzyloxy-hept-6-en-2-ol 
• 162239-11-4 (2S,3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-hept-6-en-2-ol 
• 129173-16-6 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 162239-12-5 3,6-anhydro-4,5,7-tri-O-benzyl-1,2-dideoxy-D-gluco-hept-1-enitol 
• 92619-92-6 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 79258-18-7 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 68774-48-1 2,5-anhydro-1-O-trityl-D-mannitol 
• 492470-87-8 C₃₄H₃₂O₇ 

Downstream Products

• 102093-88-9 2,5-anhydro-3,4,6-tri-O-benzyl-1-bromo-1-deoxy-D-glucitol 
• 102208-56-0 2,5-anhydro-3,4,6-tri-O-benzyl-1-bromo-1-deoxy-D-altritol 
• 117399-54-9 4-Nitro-benzoic acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester 
• 117467-65-9 1,3,4,6-Tetra-O-benzyl-2,5-anhydro-D-mannitol 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 300807-68-5 Phosphoric acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester 
• 109065-80-7 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-D-mannitol 
• 94273-27-5 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose 
• 583826-63-5 C₅₄H₅₆O₈ 
• 583826-67-9 C₇₄H₇₆O₁₁ 
• 52011-52-6 Phosphoric acid mono-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl) ester 
• 130466-42-1 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-diethylphosphono-6-O-diphenylphosphono-D-mannitol 
• 130372-43-9 Acetic acid (2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(diethoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester 
• 130465-01-9 ((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

A new synthetic approach to mycobacterial cell wall α-(1→5)-D-arabinofuranosyl C-oligosaccharides

Three designed arabinofuranose building blocks allowed the diastereoselective synthesis of a C-disaccharide and a C-trisaccharide by Wittig olefination. The latter compound represents the first example of all-carbon linked arabinofuranotriose analogue.

Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.

Stereoselective synthesis of tetrahydrofurans and linear methyl enol- ethers from glycals

The O-benzyl derivatives of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (D-glucal, 1), 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 7), and 1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (D-galactal, 9), underwent stereoselectively a ring contraction by treatment with thallium(III) nitrate (TTN) in MeOH, giving respectively the dimethylacetal derivatives of 3,4,6- tri-O-benzyl-2,5-anhydro-D-mannose, 3,4-di-O-benzyl-6-deoxy-2,5-anhydro-L- mannose (8) and 3,4,6-tri-O-benzyl-2,5-anhydro-D-talose (10). Conversely, the protected glycals 1, 7 and 9, underwent the ring opening reaction by action of the TTN-NaBH4 reagent in MeOH, providing the enantiomerically pure methyl enol-ethers 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-arabino-hex-1-enitol, 3,4-di-O-benzyl-2,6-dideoxy-1-O-methyl-L-arabino-hex-1-enitol and 3,4,6-tri- O-benzyl-2-deoxy-1-O-methyl-D-lyxo-hex-1-enitol. The perbenzylated glycosyl- glycals, such as 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D- glucopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (cellobial) (16), 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1,5- anhydro-2-deoxy-D-arabino-hex-1-enitol (lactal) (19) and 3,4-di-O-benzyl-6- O-(2, 3,4,6- tetra- O-benzyl- α-D-galactopyranosyl)- 1,5- anhydro-2-deoxy- D-arabino-hex-1-enitol (melibial) (22), showed the same reactivity as the corresponding glycals by reaction with TTN in MeOH, resulting selectively in the ring contracted compounds at the glycal moiety. The reaction with TTN- NaBH4 in MeOH, carried out on 16, 19 and 22, led to the formation of the open chain derivatives at the glycal site.