14233-62-6

Basic information

• Product Name: 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol
• Synonyms: 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol
• CAS NO: 14233-62-6
• Molecular Weight: 404.506
• Mol File: 14233-62-6.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol(14233-62-6)
• EPA Substance Registry System: 1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol(14233-62-6)

Safety Data

• Hazardous Substances Data: 14233-62-6(Hazardous Substances Data)

Upstream product

• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 78009-76-4 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal 
• 78009-77-5 2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose 
• 78009-78-6 (2R,3S,4R)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol 
• 13036-07-2 2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 
• 516482-68-1 N-benzyloxycarbonyl 2,3,5-tri-O-benzyl-α,β-D-arabinofuranylamine 
• 78009-79-7 Methanesulfonic acid (2R,3S,4R)-2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentyl ester 
• 73068-66-3 2,3,5-tri-O-benzyl-β-D-arabinofuranose 
• 84366-59-6 (2S,3R,4R)-2,3,5-tri-O-benzyl-pentane-1,4-diol 
• 55018-48-9 2,3,5-tri-O-benzoyl-1-deoxy-D-ribofuranose 
• 100-39-0 benzyl bromide 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 1824-96-0 methyl ribofuranoside 

Downstream Products

• 138858-60-3 4-[5-((3R,4R,5R)-4-Acetoxy-5-heptadecyl-tetrahydro-furan-3-yloxycarbonyl)-pentyl]-4-methyl-morpholin-4-ium; iodide 
• 138858-59-0 4-[5-((2R,3R,4R)-4-Acetoxy-2-heptadecyl-tetrahydro-furan-3-yloxycarbonyl)-pentyl]-4-methyl-morpholin-4-ium; iodide 
• 138858-58-9 6-Morpholin-4-yl-hexanoic acid (3R,4R,5R)-4-acetoxy-5-heptadecyl-tetrahydro-furan-3-yl ester 
• 138858-57-8 6-Morpholin-4-yl-hexanoic acid (2R,3R,4R)-4-acetoxy-2-heptadecyl-tetrahydro-furan-3-yl ester 
• 138858-51-2 (Z,1R,2S,3R)-2,3-bis(benzyloxy)-1-(heptadec-1-enyl)-oxolane 
• 78151-89-0 (2S,3S,4R)-3,4-bis(benzyloxy)tetrahydrofuran-2-carbaldehyde 
• 138858-50-1 1,4-anhydro-2,3-bis-O-benzyl-D-arabinitol 
• 138858-67-0 5-O-acetyl-1,4-anhydro-2,3-di-O-benzyl-D-arabinitol 
• 160308-13-4 1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol 
• 259137-72-9 Benzoic acid (2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 
• 160308-12-3 5-O-benzoyl-2-deoxy-1,4-O²,3-anhydro-2-<3,4-dihydro-4-oxo-1(2H)-pyrimidinyl>-D-lyxitol 
• 140623-93-4 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-arabinitol 
• 149125-44-0 Benzoic acid (2R,3R,4R)-3-methanesulfonyloxy-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 160308-10-1 1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-lyxitol 

Relevant articles and documents

Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4

Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C-C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubstituted homoallylic alcohol. Subsequent acid-catalysed cyclisation afforded the desired [5,6]-bicyclic ketal of the target molecule. This methodology was shown to be compatible with the desired E ring fragment 35 in order to construct the CDE fragment 37 of pectenotoxin-4.

Synthesis and biological properties of chemically modified siRNAs bearing 1-deoxy-d-ribofuranose in their 3′-overhang region

To elucidate the role of the sugar moiety in the two natural nucleotides of the 3′-overhang region of small interfering RNA (siRNA), we synthesized siRNAs that incorporated two abasic nucleosides, 1-deoxy-d-ribofuranose (R H). We improved the method for preparing an O-protected abasic nucleoside, 1-deoxy-2,3,5-tri-O-benzoyl-β-d-ribofuranose, via the reductive cleavage of the anomeric position of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d- ribofuranose. To incorporate RH into oligonucleotides by the standard phosphoramidite solid phase method, RH was converted into its phosphoramidite derivative and the solid support linked to a controlled pore glass resin. Chemically modified RNAs possessing RH at the 3′-overhang region were easily prepared in good yields. siRNAs containing RH showed moderate nuclease-resistance and a desirable knockdown effect.

Synthesis of fluorobenzene and benzimidazole nucleic-acid analogues and their influence on stability of RNA duplexes

Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T(m) differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene·fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ··· H H-bond.