157429-87-3

Upstream product

• 135216-47-6 5'-O,N⁶-bis(triphenylmethyl)-2',3'-secoadenosine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 173202-62-5 2',3'-Dideoxy-5'-O,N₆-bis(triphenylmethyl)-2',3'-secoadenosine-1',3'-diene 
• 157429-93-1 3'-Chloro-2',3'-dodeoxy-N₆-(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-92-0 3'-Azido-2',3'-dideoxy-N₆-(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-90-8 3'-Chloro-2',3'-dideoxy-5'-O,N₆-bis(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-89-5 3'-Azido-2',3'-dideoxy-5'-O,N₆-bis(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-91-9 2'-Deoxy-5'-O,N₆-bis(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-94-2 2'-Deoxy-N₆-(triphenylmethyl)-2',3'-secoadenosin-1'-ene 
• 157429-88-4 2'-Deoxy-3'-O-<(tol-4-yl)sulfonyl>-5'-O,N6-bis(triphenylmethyl)-2',3'-secoadenosin-1'-ene 

Relevant academic research and scientific papers

A novel type of unsaturated seconucleoside analogues

1',2'-Unsaturated secoadenosine 3-6 and secouridine 15, 16 analogues were synthesized by the base promoted regioselective elimination of corresponding 2',3'-ditosylates. Efficient and selective O-detrilation of these acid sensitive compounds was achieved by ZnBr2 in dichloromethane.

Syntheses and reactions of 1',2'-unsaturated 2',3'-seconucleoside analogues

The 1',2'-unsaturated 2',3'-secoadenosine and 2',3'-secouridine analogues were synthesized by the regioselective elimination of the corresponding 2',3'-ditosylates, 2 and 18, respectively, under basic conditions. The observed regioselectivity may be explained by the higher acidity and, hence, preferential elimination of the anomeric H-C(1') in comparison to H-C(4'). The retained (tol-4-yl)sulfonyloxy group at C(3') of 3 allowed the preparation of the 3'-azido, 3'-chloro, and 3'-hydroxy derivatives 5-7 by nucleophilic substitution. ZnBr2 in dry CH2Cl2 was found to be successful in the removal (85%) of the trityl group without any cleavage of the acid-sensitive, ketene-derived N,O-ketal function. In the uridine series, base-promoted regioselective elimination (→ 19), nucleophilic displacement of the tosyl group by azide (→ 20), and debenzylation of the protected N(3)-imide function gave 1',2'-unsaturated 5'-O-trityl-3'-azido-secouridine derivative 21. The same compound was also obtained by the elimination performed on 2,2'-anhydro-3'-azido-3'-deoxy-5'-O-trityl-2',3'-secouridine (22) that reacted with KO(t-Bu) under opening of the oxazole ring and double-bond formation at C(1').