676598-19-9

Basic information

• Product Name: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside
• Synonyms: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside
• CAS NO: 676598-19-9
• Molecular Weight: 266.294
• Mol File: 676598-19-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside(676598-19-9)
• EPA Substance Registry System: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside(676598-19-9)

Safety Data

• Hazardous Substances Data: 676598-19-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 452-51-7 D-2-deoxyribose 
• 874-60-2 4-methyl-benzoyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 

Downstream Products

• 4449-43-8 α-deoxythymidine 
• 78137-97-0 1-<3-O-benzyl-2-deoxy-5-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione 
• 78138-04-2 1-<3-O-benzyl-2-deoxy-5-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl>thymine 
• 35898-26-1 4-Methyl-benzoic acid (2R,3S,5S)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 78137-96-9 1-O-acetyl-3-O-benzyl-2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranose 
• 78138-12-2 4-Methyl-benzoic acid (2R,3S)-3-benzyloxy-5-chloro-tetrahydro-furan-2-ylmethyl ester 
• 676598-25-7 4-Methyl-benzoic acid (R)-5,5-bis-benzylsulfanyl-3,3-difluoro-2-trifluoromethanesulfonyloxy-pentyl ester 
• 676598-32-6 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine 
• 676598-33-7 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-α-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine 
• 676598-28-0 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-α/β-L-ribofuranosyl]uracil 
• 676598-26-8 benzyl-2,3-dideoxy-3,3-difluoro-1,4-dithio-5-O-toluoyl-L-furanoside 

Relevant articles and documents

Synthesis and DNA/RNA Binding Properties of Conformationally Constrained Pyrrolidinyl PNA with a Tetrahydrofuran Backbone Deriving from Deoxyribose

Sugar-derived cyclic β-amino acids are important building blocks for designing of foldamers and other biomimetic structures. We report herein the first synthesis of a C-activated N-Fmoc-protected trans-(2S,3S)-3-aminotetrahydrofuran-2-carboxylic acid as a building block for Fmoc solid phase peptide synthesis. Starting from 2-deoxy-d-ribose, the product is obtained in a 6.7% overall yield following an 11-step reaction sequence. The tetrahydrofuran amino acid is used as a building block for a new peptide nucleic acid (PNA), which exhibits excellent DNA binding affinity with high specificity. It also shows preference for binding to DNA over RNA and specifically in the antiparallel orientation. In addition, the presence of the hydrophilic tetrahydrofuran ring in the PNA structure reduces nonspecific interactions and self-aggregation, which is a common problem in PNA due to its hydrophobic nature.