111550-00-6

Upstream product

• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 111549-99-6 5-O-allyl-2,3,4-tri-O-benzyl-1-O-(β-D-ribofuranosyl)-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 
• 100-39-0 benzyl bromide 
• 111549-97-4 2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol 
• 111549-98-5 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 
• 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 
• 5336-08-3 D-Ribono-1,4-lactone 

Downstream Products

• 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 
• 111550-03-9 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-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 
• 111550-04-0 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 

Relevant academic research and scientific papers

SYNTHESIS OF FRAGMENTS OF THE CAPSULAR POLYSACCHARIDE OF HAEMOPHILUS INFLUENZAE TYPE B, COMPRISING TWO OR THREE REPEATING UNITS

The synthesis of the ribosyl-ribitol derivatives 15 and 17 (Scheme 2) is presented.The compounds served as building blocks for the preparation of protected fragments (24, n=1 or 2; Fig. 2) of the title polysaccharide.The bifunctional reagent bis-2-chlorophenylphosphate (18, Fig. 2) was used for all phosphorylation reactions.Attachment to a spacer and complete deprotection of the products, to afford 25 (n=2 or 3), is described.

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.