Daniel 11:16-20
Daniel 11:16
But he that cometh against him shall do according to his own will, and none shall stand before him: and he shall stand in the glorious land, which by his hand shall be consumed.
The one who was coming was Antiochus the Great.  He took the land of Judah away from the Egyptians.  Judah and Jerusalem had passed from the king of the south to the king of the north.  Antiochus had the military strength to completely destroy the land of Judah but he did not do it.  In fact, he gave the Jews of the land many privileges and support.
Daniel 11:17
He shall also set his face to enter with the strength of his whole kingdom, and upright ones with him; thus shall he do: and he shall give him the daughter of women, corrupting her: but she shall not stand on his side, neither be for him.
After Antiochus won the victory at Paneas in 198 B.C. the treaty which gave him Syria and Palestine was sealed by a marriage between his daughter Cleopatra (not the one of Roman fame) and Ptolemy V Epiphanes who was now 7 year old.  The marriage would take place 5 years later in 193 B.C. at Raphia.   Two years later Antiochus was defeated by the Romans in 191 B.C at Thermopylae and at Magnesus in 190 B.C.  The Seleucids had continued to rule Judea until 142 B.C.  Cleopatra sent a letter of congratulations to the Romans showing she did not stand by her father.
Daniel 11:18
After this shall he turn his face unto the isles, and shall take many: but a prince for his own behalf shall cause the reproach offered by him to cease; without his own reproach he shall cause it to turn upon him.
In 198 B.C Antiochus the Great took his army along the coast of the Mediterranean Sea and within a year had conquered Asia Minor.  After that he conquered Macedonia, Hellas, and Thrace.  He disrespected the Romans and this caused them to send General Lucius Scipio Asiaticus against him.  He defeated Antiochus and forced him to sign a peace treaty at Apamea in 188 B .C.   So the reproach turned back on Antiochus caused him to be driven from Thermopylae and he had to give Asia Minor to the Romans.
Daniel 11:19
Then he shall turn his face toward the fort of his own land: but he shall stumble and fall, and not be found.
In 187 B.C. Antiochus the Great was attempting to plunder the temple of Belus in Elymais.  It was a pagan temple of Jupiter in Babylon near Susa (Shushan).  It was located at the head of the Persian Gulf.  While he was trying to plunder this temple, he and his soldiers were slain by the citizens of that town.  He never returned to Syria.
Daniel 11:20
Then shall stand up in his estate a raiser of taxes in the glory of the kingdom: but within few days he shall be destroyed, neither in anger, nor in battle.
After the death of Antiochus the Great, his son, also his successor, Seleucus IV Philopater (187-175 B.C.) had inherited much debt as a result of the treaty of Apamea.  The Romans wanted an annual tribute of one thousand talents.  It is not sure if this was talents of gold or silver.  Either way it was a huge tax on the people of Judah.  He also burdened his own subjects with continual heavy taxes.  He made a big mistake in that he sent his finance minister, Heliodorus, to Jerusalem to raid the temple treasury.  It is believed that Heliodorus poisoned Seleucus and he died in 175 B.C.