Hetero-polyoxime compounds and their preparation by parallel assembly

A homogeneous hetero-polyoxime composition produced by a process comprising the steps of:

• 1) obtaining a first organic baseplate molecule having present therein a plurality of at least three first orthogonal reactive groups capable of oxime linkage formation,
• 2) obtaining a second organic molecule having present therein a second orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate,
• 3) obtaining a third organic molecule having present therein a third orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate, wherein said third organic molecule and said second organic molecule are different, wherein said first orthogonal reactive groups, said second orthogonal reactive groups and said third orthogonal reactive groups are independently selected from the group consisting of an aldehyde group, a keto group and an amino-oxy group and wherein said second orthogonal reactive groups and said third orthogonal reactive groups are not complementary to the same first orthogonal reactive groups,
• 4) mixing the baseplate molecules and the second organic molecules under conditions allowing essentially quantitative oxime linkage formation between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive groups on the baseplate molecules but not between the second orthogonal reactive group of said second organic molecules and first orthogonal reactive groups on the baseplate molecules complementary to the third orthogonal reactive group on said third organic molecule, whereby oxime linkage formation occurs between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 5) mixing the baseplate molecules and the third organic molecules, either contemporaneously or sequentially with said mixing in step 4), under conditions allowing essentially quantitative oxime linkage formation between the third orthogonal reactive group of said third organic molecules and at least one of said first orthogonal reactive groups on the baseplate molecules but not between the third orthogonal reactive group of said third organic molecules and the first orthogonal reactive groups on the baseplate molecules complementary to the second orthogonal reactive group on said second organic molecules, whereby oxime linkage formation occurs between the third orthogonal reactive group of said third organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 6) optionally repeating steps 2 and 4 with one or more additional organic molecules having present therein an orthogonal reactive group capable of oxime linkage formation with its complementary first orthogonal reactive groups on the baseplate, and
• 7) separating the hetero-polyoxime product from unreacted organic molecules.

A method of producing a homogeneous hetero-polyoxime composition comprising the steps of:

• 1) obtaining a first organic baseplate molecule having present therein a plurality of at least three first orthogonal reactive groups capable of oxime linkage formation,
• 2) obtaining a second organic molecule having present therein a second orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate,
• 3) obtaining a third organic molecule having present therein a third orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate, wherein said third organic molecule and said second organic molecule are different, wherein said first orthogonal reactive groups, said second orthogonal reactive groups and said third orthogonal reactive groups are independently selected from the group consisting of an aldehyde group, a keto group and an amino-oxy group and wherein said second orthogonal reactive groups and said third orthogonal reactive groups are not complementary to the same first orthogonal reactive groups,
• 4) mixing the baseplate molecules and the second organic molecules under conditions allowing essentially quantitative oxime linkage formation between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive groups on the baseplate molecules but not between the second orthogonal reactive group of said second organic molecules and first orthogonal reactive groups on the baseplate molecules complementary to the third orthogonal reactive group on said third organic molecule, whereby oxime linkage formation occurs between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 5) mixing the baseplate molecules and the third organic molecules, either contemporaneously or sequentially with said mixing in step 4), under conditions allowing essentially quantitative oxime linkage formation between the third orthogonal reactive group of said third organic molecules and at least one of said first orthogonal reactive groups on the baseplate molecules but not between the third orthogonal reactive group of said third organic molecules and the first orthogonal reactive groups on the baseplate molecules complementary to the second orthogonal reactive group on said second organic molecules, whereby oxime linkage formation occurs between the third orthogonal reactive group of said third organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 6) optionally repeating steps 2 and 4 with one or more additional organic molecules having present therein an orthogonal reactive group capable of oxime linkage formation with its complementary first orthogonal reactive groups on the baseplate, and
• 7) separating the hetero-polyoxime product from unreacted organic molecules.

A method of producing a homogeneous hetero-polyoxime composition comprising the steps of:

• 1) obtaining a first organic baseplate molecule having present therein a plurality of at least three first orthogonal reactive groups capable of oxime linkage formation,
• 2) obtaining a second organic molecule having present therein a second orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate,
• 3) obtaining a third organic molecule having present therein a third orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate, wherein said third organic molecule and said second organic molecule are different, and wherein said first orthogonal reactive groups, said second orthogonal reactive groups and said third orthogonal reactive groups are selected from the group consisting of an aldehyde group, a keto group and an amino-oxy group,
• 4) mixing the baseplate molecules and the second organic molecules under conditions allowing essentially quantitative oxime linkage formation between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive groups on the baseplate molecules, whereby oxime linkage formation occurs between the second orthogonal reactive group of said second organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 5) isolating a homogeneous oximation product of step 4,
• 6) mixing said isolated homogeneous oximation product and the third organic molecules, under conditions allowing essentially quantitative oxime linkage formation between the third orthogonal reactive group of said third organic molecules and at least one first orthogonal reactive groups remaining on the homogeneous oximation product, whereby oxime linkage formation occurs between the third orthogonal reactive group of said third organic molecule and at least one of said first orthogonal reactive group on said baseplate molecule,
• 7) optionally repeating steps 2, 4 and 5 with one or more additional organic molecules having present therein an orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate, and
• 8) separating the hetero-polyoxime product from unreacted organic molecules.

A method of producing a library of hetero-polyoxime compounds comprising the steps of:

• 1) obtaining a first organic baseplate molecule having present therein a plurality of at least three first orthogonal reactive groups capable of oxime linkage formation,
• 2) obtaining a plurality of second organic molecules, each having present therein a second orthogonal reactive group capable of oxime linkage formation with at least one of said first orthogonal reactive groups on the baseplate molecule, wherein said plurality of second organic molecules comprises at least two different second organic molecules, wherein said first orthogonal reactive groups, and said second orthogonal reactive groups are selected from the group consisting of an aldehyde group, a keto group and an amino-oxy group,
• 3) mixing the baseplate molecule and the plurality of second organic molecules under conditions allowing essentially quantitative oxime linkage formation between the second orthogonal reactive group on the second organic molecules and the complementary first orthogonal reactive groups on the baseplate molecule, whereby oxime linkage formation occurs between the second orthogonal reactive group of said second organic molecule and the complementary first orthogonal reactive group on said baseplate molecule, and
• 4) isolating the library produced.