153186-11-9

Upstream product

• 100-39-0 benzyl bromide 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 473290-44-7 1-({(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane 
• 100-44-7 benzyl chloride 
• 212970-72-4 {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 

Downstream Products

• 473290-51-6 (E)-3-((2S,3R,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-oxo-tetrahydro-furan-2-yl)-acrylic acid methyl ester 
• 473290-50-5 (E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester 
• 473290-49-2 methyl (2E)-3-{(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}prop-2-enoate 
• 473290-53-8 (E)-3-[(2S,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-yl]-acrylic acid methyl ester 
• 473290-57-2 methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate 
• 473290-55-0 methyl (2E)-3-{(2S,3S)-5-oxo-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-4(Z)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate 
• 473290-47-0 (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 

Relevant academic research and scientific papers

Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)- and (3S)-3-hydroxy-4,4-disubstituted heptono-1,4-lactones as protein kinase C (PK-C) ligands with increased hydrophilicity

The stereospecific introduction of (R)- and (S)-OH groups at position C-3 of two diacylglycerol γ-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH groups were introduced following two different diastereoselective multistep syntheses starting from diacetone-D-glucose. The PK-C binding affinities for the new compounds were weaker in comparison to those of the parent compounds, suggesting that the extra OH does not engage efficiently in hydrogen bonding at the receptor.

Oligonucleotides containing novel 4'-C- or 3'-C-(aminoalkyl)-branched thymidines

The synthesis of four novel 3'-C-branched and 4'-C-branched nucleosides and their transformation into the corresponding 3'-O-phosphoramidite building blocks for automated oligonucleotide synthesis is reported. The 4'-C-branched key intermediate 11 was synthesized by a convergent strategy and converted to its 2-O-methyl and 2'-deoxy-2'-fluoro derivatives, leading to the preparation of novel oligonucleotide analogues containing 4'-C-(aminomethyl)-2'-O-methyl monomer X and 4'-C-(aminomethyl)-2'-deoxy-2'-fluoro monomer Y (Schemes 2 and 3). In general, increased binding affinity towards complementary single- stranded DNA and RNA was obtained with these analogues compared to the unmodified references (Table 1). The presence of monomer X or monomer Y in a 2'-O-methyl-RNA oligonucleotide had a negative effect on the binding affinity of the 2'-O-methyl-RNA oligonucleotide towards DNA and RNA. Starting from the 3'-C-allyl derivative 28, 3'-C-(3-aminopropyl)-protected nucleosides and 3'- O-phosphoramidite derivatives were synthesized, leading to novel oligonucleotide analogues containing 3'-C-(3-aminopropyl)thymidine monomer Z or the corresponding 3'-C-(3-aminopropyl)-2'-O,5-dimethyluridine monomer W (Schemes 4 and 5). Incorporation of the 2'-deoxy monomer Z induced no significant changes in the binding affinity towards DNA but decreased binding affinity towards RNA, while the 2'-O-methyl monomer Z induced decreased binding affinity towards DNA as well as RNA complements (Table 2).

Synthesis of 4'-C-methylnucleosides.

Several 4'-C-methylnucleosides were prepared. 1H-NMR studies on these nucleotides showed that they have the 3'-exo furanose ring conformation different from the 3'-endo conformation of natural nucleosides.