Processes and intermediates for phosphorous-containing covalent

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 253, 556436, 556449, C07H 2100, C07H 2102

Patent

active

061244503

ABSTRACT:
Synthetic processes are provided wherein substituted silylalkyl phosphoramidites serve as coupling reagents for preparing phosphate, phosphorothioate, and other phosphorous-containing covalent linkages. Also provided are synthetic intermediates useful in such processes.

REFERENCES:
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4725677 (1988-02-01), Koster et al.
patent: 4845205 (1989-07-01), Huynh Dinh et al.
patent: 4910300 (1990-03-01), Urdea et al.
patent: 5113005 (1992-05-01), Celebuski
patent: 5159095 (1992-10-01), Celebuski
patent: 5614621 (1997-03-01), Ravikumar et al.
Alul et al., "Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives", Nucl. Acids. Res., 1991, 19, 1527-1532.
Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach", Tetrahedron, 1992, 48, 2223-2311.
Celebuski, et al., "Synthesis and Utility of a DNA Phosphorylating Agent Based on 2-(Triphenylsilyl)ethanol", J. Org. Chem., 1992, 57, 5535-5538.
Honda, et al., "2-Diphenylmethylsilylethyl Group as a New Protecting Group of Internucleotidic Phosphates in Oligonucleotide Synthesis", Tetrahedron Letters, 1981, 2093-2096.
Iyer et al., "3H-1,2-Benzodithiole-3-one 1,1-Dioxide as an Improved Sulfurizing Reagent in the Solid-Phase Synthesis of Oligodeoxyribonucleoside Phosphorothioates", J. Am. Chem. Soc., 1990, 112, 1253-1254.
Iyer et al., "The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfur-Transfer Reagent", J. Org. Chem., 1990, 55, 4693-4699.
Kamer et al., "An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters Via the Schonberg Reaction", Tetra. Lett., 1989, 30, 6757-6760.
March, "Advanced Organic Chemistry", John Wiley & Sons, New York, Third Edition, 1985, Chapter 1, pp. 16-18 and Chapter 9, pp. 237-239.
Rao et al., "Dibenzoyl Tetrasulphide--A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides", Tetra. Lett., 1992, 33, 4839-4842.
Streitwieser and Heathcock, "Introduction to Chemistry", Second Edition, 1981, Chapter 15, 437-440.
Takaku, et al., "Use of 1,1,1,3,3,3-Hexafluoro-2-Propyl Protecting Group in the Synthesis of DNA Fragments Via Phosphoramidite Intermediates", Tetrahedron Letters, 1988, 29, 81-84.
Vu et al., "Internucleotide Phosphite Sulfurization with Tetraethyl Thiuram Disulfide. Phosphorothioate Oligonucleotide Synthesis Via Phosphoramidite Chemistry", Tetra. Lett., 1989, 32, 3005-3008.
Wright et al., "Large Scale Synthesis of Oligonucleotides via Phosphoramidite Nucleosides and a High-Loaded Polystyrene Support", Tetra. Lett., 1993, 32, 3373-3376.
Sawabe et al., "Use of 2-Trimethylsilylethyl as a Protecting Group in Phosphate Monoester Synthesis", Tetra. Lett., 1992, 33(50), 7685-7686.
Hartle, R.J., "Structural Stabilities of the Trimethylsilylmethyl and Neopentyl Groups in the Preparation of Phosphonyl Dichlorides", J. Org. Chem., 1966, 31, 4288-4290.
Kawashima, T. et al., "Fluoride Ion-Induced Horner-Emmons Reaction of .alpha.-Silylalklphosphonic Derivatives with Carbonyl Compounds", Bull. Chem. Soc. Japan, 1987, 60, 1131-1137.
Sonnek, G. et al., "Aluminum alkyls with heteroatoms; preparation of phosphonic acid diamides. Part XI", Chem. Abstracts, 1981, 95, 95:204061, p. 694.
Ravikumar, V.T. et al., "Synthesis of Oligonucleotides Via Phosphoramidite Approach Utilizing 2-Diphenylmethylsilyethyl (DPSE) as a Phosphorus Protecting Group", Tetrahedron, 1994, 50(31), 9255-9266.
Ravikumar, V.T. et al., "2-Diphenylmethylsilyethyl (DPSE): a versatile protecting group for oligodeoxyribonucleotide synthesis", Gene, 1994, 149, 157-161.
Sawabe, A. et al., "Use of 2-Trimethylsilylethyl as a Protecting Group in Phosphate Monoester Synthesis", Tetra. Lett., 1992, 33(50), 7685-7686.
Wada et al., "2-(Trimethylsilyl)ethyl as a Phosphate Protecting Group in Oligonucleotide Synthesis", Tetra. Lett., 1994, 35(5), 757-760.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Processes and intermediates for phosphorous-containing covalent does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Processes and intermediates for phosphorous-containing covalent , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Processes and intermediates for phosphorous-containing covalent will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2101222

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.