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No, you can't do that. While Transit Gateway supports attachments (VPCs, VPN, Direct Connect, other Transit Gateways, etc.) that have the same CIDR range you can't route to both of them (i.e. the same CIDR range) within a single route table.
If you imagine a world where you could do that (have a route for CIDR range A that points to destination X and destination Y), how would you route packets to A? Do you send packet 1 to X and packet 2 to Y and so on? If so, that would break your communications pretty badly.
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