Phosphoramidite compounds and process for production thereof

Details Phosphoramidite compounds and process for production thereof Phosphoramidite compounds and process for production thereof

1988-08-04

1991-06-25

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 28, 536 29, C07H 19167, C07H 19173

Patent

active

050268384

ABSTRACT:
Phosphoramidite compounds of the general formula ##STR1## wherein each of R.sub.1 and R.sub.2 represents a hydroxyl group having a protective group, or the group --OR.sub.4, R.sub.3 represents a hydrogen atom, a hydroxyl group having a protective group, or the group --OR.sub.4, R.sub.4 represents the group ##STR2## X represents a secondary amino group, R.sub.5 represents an allylic residue or a protective group capable of being split off by beta-cleavage, and B.sup.AOC represents a nucleoside base residue in which the amino or imino group is protected with an allyloxycarbonyl-type residue, with the proviso that only one of R.sub.1, R.sub.2 and R.sub.3 represents the group--OR.sub.4. The compounds can be produced by reacting a nucleoside represented by the general formula ##STR3## wherein each of R.sub.1 ' and R.sub.2 ' represents a hydroxyl group which may have a protective group, R.sub.3 ' represents a hydrogen atom, or a hydroxyl group which may have a protective group, and B.sup.AOC is as defined, with the proviso that only one of R.sub.1 ', R.sub.2 'and R.sub.3 ' is a hydroxyl group,
with a phosphoramide compound represented by the general formula ##STR4## wherein X and R.sub.5 are as defined, and Y represents a secondary amino group or a halogen atom.

REFERENCES:
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Hayakawa, et al., Journal of Organic Chemestry, vol. 51, No. 12, "Allyloxycarbonyl Group: A Versatile Blocking Group for Nucleotide Synthesis", pp. 2400-2402, 1986.
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Guibe, et al., Tetrahedron Letters, vol. 22, No. 37, "The Allyloxy-carbonyl Group for Alcohol Protection: Quantitative Removal or Transformation into Allyl Protecting Group Via Pi-allyl Complexes of Palladium", pp. 3591-3594, 1981.
Kunz, et al., Agnew. Chem. Int. Ed. Engl, vol. 23, No. 6, "The Allyl-Carbonyl (Aloc) Moiety-conversion of an Unsuitable Into a Valuable Amino Protecting Group for Peptide Synthesis", pp. 436-437, 1984.
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