111549-98-5

Basic information

• Product Name: 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol
• Synonyms: 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol
• CAS NO: 111549-98-5
• Molecular Weight: 907.027
• Mol File: 111549-98-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol(111549-98-5)
• EPA Substance Registry System: 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol(111549-98-5)

Safety Data

• Hazardous Substances Data: 111549-98-5(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 5336-08-3 D-Ribono-1,4-lactone 
• 111549-97-4 2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 111549-96-3 5-O-allyl-2,3,4-tri-O-benzyl-1-O-trityl-D-ribitol 
• 111549-95-2 5-O-allyl-1-O-trityl-D-ribitol 
• 111549-92-9 5-O-(allyloxycarbonyl)-2,3-O-isopropylidene-D-ribonolactone 
• 111549-93-0 5'-O-allyl-2',3'-O-isopropylidene-D-ribonic-γ-lactone 
• 111549-94-1 5-O-allyl-2,3-O-isopropylidene-D-ribitol 

Downstream Products

• 111550-03-9 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol 
• 111550-00-6 5-O-allyl-2,3,4-tri-O-benzyl-1-O-<3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol 
• 111550-02-8 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol 
• 111642-10-5 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-5-O-(trans-propen-1-yl)-D-ribitol 
• 111550-01-7 5-O-allyl-2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol 
• 111550-04-0 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol 
• 111549-99-6 5-O-allyl-2,3,4-tri-O-benzyl-1-O-(β-D-ribofuranosyl)-D-ribitol 

Relevant articles and documents

SYNTHESIS OF RIBOFURANOSIDES BY CATALYSIS WITH LEWIS ACIDS. GLYCOSIDATION VERSUS TRANSACETYLATION

Several ribofuranosyl derivatives bearing trichloroacetimidoyl or acetyl leaving groups in a Lewis acid promoted ribosylation reaction were prepared and used in an attempt to improve the yield and to avoid donor -> acceptor transacetylation.Trichloroaceti

Synthesis of fragments of the capsular polysaccharide of Haemophilus influenzae type b. Part I. Preparation of suitably protected 1-O-β-d-ribofuranosyl-d-ribitol building blocks

The synthesis of the protected ribosylribitol derivatives 15 and 17, which are building blocks for the preparation of fragments of the H. influenzae type b polysaccharide, is presented. Starting from d-ribonolactone (1), 5-O-allyl-2,3,4-tri-O-benzyl-d-ribitol (8) was prepared in seven steps (Scheme 1). Coupling of 8 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (9) in the presence of trimethylsilyl trifluoromethanesulfonate gave the ribosylribitol derivative 10 (Scheme 2), which was debenzoylated to afford compound 11. The C-3′- and C-5′-hydroxyl functions of the ribose moiety of 11 were protected with the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl group and the C-2′ position with the benzyloxymethyl group. Compound 13 thus obtained was converted into its 5-O-trans-1-propenyl isomer 14. Cleavage of the propenyl group from 14 gave compound 15, which can be phosphorylated at O-5 of the ribitol. On the other hand, removal of the 3′,5′-protection from 14 and subsequent blocking of the primary hydroxyl function yielded ribosylribitol derivative 17 having a 3′-hydroxyl function available for phosphorylation.