Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid
The invention provides a glucoside compound, which is capable of providing a phosphoramidite, which can be produced at low cost and can produce a nucleic acid in high yield and with high purity. The glycoside compound has the formula wherein B, R1, R2, and R3 are as described herein.
1. An ether represented by the following chemical formula (106):
in the aforementioned chemical formula (106),
R 4 is a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group,
n is a positive integer,
L 1 is an ethylene group (—CH 2 CH 2 —), wherein hydrogen atoms besides a hydrogen atom bonded to the α-position relative to [D 1 ] are optionally substituted by a straight chain or branched alkyl group, and
[D 1 ] is an electron-withdrawing group,
an enantiomer thereof, a tautomer or stereoisomer thereof or a salt thereof.
2. A method of producing the ether according to claim 1 , comprising a coupling reaction of a thioether represented by the following chemical formula (103) and an alcohol represented by the following chemical formula (105), in the presence of a halogenating agent and a Lewis acid,
in the aforementioned chemical formulas (103) and (105),
R 4 is as defined for the aforementioned chemical formula (106),
R 5 is a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group, which may be the same as or different from R 4 ,
in the aforementioned chemical formula (103),
n is as defined for the aforementioned chemical formula (106), and
in the aforementioned chemical formula (105),
L 1 and [D 1 ] are as defined for the aforementioned chemical formula (106).
3. The production method according to claim 2 , wherein the aforementioned halogenating agent is at least one selected from the group consisting of N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, iodine, bromine and chlorine.
4. The production method according to claim 2 , wherein the aforementioned Lewis acid is at least one selected from the group consisting of perfluoroalkylcarboxylic acid, perfluoroalkylsulfonic acid, alkylsulfonic acid and a salt thereof.
5. The production method according to claim 2 , wherein the aforementioned Lewis acid is a silver salt of trifluoromethanesulfonic acid.
6. The production method according to claim 2 , wherein the aforementioned coupling reaction is performed in the co-presence of molecular sieve.
7. The production method according to claim 6 , further comprising a step of producing the thioether represented by the chemical formula (103) by the production method comprising a coupling reaction of thiol or thioalkoxide represented by the chemical formulas (101a) and (101b) with a halide represented by the chemical formula (102) to give a thioether represented by the chemical formula (103):
wherein
in the aforementioned chemical formulas (101a), (101b) and (103),
R 4 and R 5 are each a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group, which may be the same or different,
in the aforementioned chemical formulas (101a) and (101b),
M 1 and M 2 may be the same or different and each is a hydrogen atom or a metal,
in the aforementioned chemical formulas (102) and (103),
n is a positive integer, and
in the aforementioned chemical formula (102),
X 1 and X 2 may be the same or different and each is halogen.
8. The production method according to claim 7 , wherein, in the aforementioned chemical formulas (101a), (101b) and (103), R 4 and R 5 are each a methyl group.