26685-74-5

Basic information

• Product Name: Benzyl 3-O,4-O-isopropylidene-β-L-ribopyranoside
• Synonyms: Benzyl 3-O,4-O-isopropylidene-β-L-ribopyranoside
• CAS NO: 26685-74-5
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.3163
• Mol File: 26685-74-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzyl 3-O,4-O-isopropylidene-β-L-ribopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 3-O,4-O-isopropylidene-β-L-ribopyranoside(26685-74-5)
• EPA Substance Registry System: Benzyl 3-O,4-O-isopropylidene-β-L-ribopyranoside(26685-74-5)

Safety Data

• Hazardous Substances Data: 26685-74-5(Hazardous Substances Data)

Upstream product

• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 7296-55-1 L-arabinose 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 100-51-6 benzyl alcohol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 87-72-9 L-ribose 
• 389086-19-5 (3aS,6S,7S,7aS)-6-benzyloxy-2,2-dimethyl-7-(tert-butyldimethylsilyl)oxy-tetrahydro-1,3-dioxolo[4,5-c]pyran 
• 500564-92-1 (2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal 
• 389085-95-4 (4R,5R,6S,7S)-5-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-4-methylocten-2-one 
• 389085-87-4 2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane 
• 389085-88-5 1-[10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyl)oxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-5-(tert-butyldimethylsilyl)oxy-5-[5-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylpentan-2-one 
• 389085-89-6 [1R,1(4S,5S),2R,5E,14R,17S]-19-benzyloxy-1,14-bis(tert-butyldimethylsilyloxy)-1-[5-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,14-dimethyl-17-(triethylsilyl)oxy-5-nonadecene-4,10,13-trione 
• 389086-31-1 C₇₁H₁₁₈O₉S₂Si₄ 
• 389086-30-0 C₇₁H₁₂₀O₉S₂Si₄ 
• 389085-96-5 [1R,1(4S,5S),2R,5E,9(3S,4R,7S)]9-{2-[9-benzyloxy-4-(tert-butyldimethylsilyl)oxy-3-(4-methoxybenzyl)oxy-4-methyl-7-(triethylsilyl)oxynonyl]-1,3-dithian-2-yl}-1-(tert-butyldimethylsilyloxy)-1-[5-(tert-butydiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan] 
• 389086-14-0 C₇₉H₁₃₀O₁₁S₂Si₄ 
• 389086-22-0 (3E,5R,6S,7S)-5-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-3-octen-2-one 
• 500564-86-3 ethyl (2E,4R,5S,6S)-4-(tert-butyldimethylsilyl)-oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylene-dioxy)-2-heptenoate 
• 389086-21-9 (2E,4R,5S,6S)-N-methoxy-N-methyl-4-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-2-heptenamide 

Relevant articles and documents

A solid-phase approach to novel purine and nucleoside analogs

This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbrueggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective oxidation-reduction procedure of the 2-OH group. Some compounds exhibited moderate activity against HIV-1 in PBM cells.

A practical synthesis of L-FMAU from L-arabinose

A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.