The Kremlin has put itself in conflict with the West as it shields the regime from United Nations sanctions and continues to provide weapons even as others impose arms embargoes.

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MOSCOW — Russia’s defiance of international efforts to end Syrian President Bashar Assad’s crackdown on protests is rooted in a calculation that it can keep a Mideast presence by propping up its last remaining ally in the region — and has nothing to lose if it fails.

The Kremlin has put itself in conflict with the West as it shields Assad’s regime from United Nations sanctions and continues to provide it with weapons even as others impose arms embargoes.

With the United States and its allies pressing Assad to step down, the Arab League last week issued a detailed plan for a political transition in Syria. The plan was welcomed by the Obama administration, and Arab leaders quickly said they would refer it to the United Nations.

And a day later, Russia had its say: Not a chance.

“This is an effort from the Arab League, if I understand correctly, to sort of already put a precooked solution on the table,” said Vitaly Churkin, Russia’s envoy to the United Nations.

The response fell into a familiar pattern by which Russia has shown a growing willingness to challenge the United States and its European partners on a range of issues. In recent weeks, Russia has sought U.N. scrutiny of possible crimes by NATO during its air campaign in Libya, and even called for investigations into illicit human-organ sales in Kosovo, a close ally of the West. Most notably, Russia has obstructed any effort to increase pressure on Iran.

Critics say Russia’s tough line at the United Nations reflects what one senior council diplomat described as “the Putinization of Russian foreign policy,” on the eve of what many expect will be the return of Prime Minister Vladimir Putin to the presidency. Other analysts say Russia is trying to reassert its authority in the council following a period in which the United States and Europe prevailed in the handling of several major crises, engineering the downfall of former Ivory Coast leader Laurent Gbagbo and, more recently, of Moammar Gadhafi in Libya.

“The Russians looked diminished in the first half of 2011 and the strategy is to show, one, they are prepared to act as a spoiler, but, two, they can also lay out a more proactive agenda,” said Richard Gowan, an expert on the United Nations at the New York University Center for International Cooperation.

Defying United States

Russia’s relations with the U.S. are already strained amid controversy over U.S. missile-defense plans and other disputes. And Prime Minister Putin seems eager to defy the U.S. as he campaigns to reclaim the presidency in March elections.

Russia is coming under mounting pressure to break with Assad from the Arab League, which is sending a delegation to the Security Council on Tuesday to press its case for a political transition that would require the Syrian leader step aside. Meantime, Morocco, acting on behalf of a group of Western and Arab governments, has introduced a draft resolution endorsing the Arab League initiative calling on states to follow the Arab organization’s example by imposing sanctions on Syria. The Russians have responded coolly.

The high-level diplomatic gamesmanship is playing out as violence continues to spiral in Syria, forcing the United States to prepare for the possible closure of its embassy and the evacuation of its diplomatic personnel. U.N. officials estimate that more than 5,400 civilians have been killed, mostly at the hands of government security forces, since protesters took to the streets earlier last year.

Russia’s stance underscores the strength and depth of its relationship with Assad’s regime, which is not only a recipient of Russian arms but also host of a Russian naval base. The crisis in Syria also has provided Moscow with an opportunity to show it is a more reliable ally than Western powers, particularly the United States, which is seen by many in the region as having abandoned one of its closest allies, former Egyptian leader Hosni Mubarak.

Churkin said Russia’s concerns about the Libya mission were legitimate, asserting that the killing of civilians during the NATO campaign was “a real issue.”

Russia, along with Brazil, China, India and South Africa, believe “it would be extremely dangerous if” the West continues to be “carried away by this regime-change idea,” he said.

In Syria, Russia has pursued a complicated diplomatic strategy to shore up the regime, joining China in vetoing the Western-backed resolution threatening sanctions against Syria, and introducing its own resolution that would allow Assad’s army to still be armed.

Asked if Russia’s ongoing arms sales to Assad’s government were perhaps undercutting his government’s effort to pursue a political settlement, Churkin said: “We are not doing anything which is contrary to international law. Other than that, we don’t have to give any explanation to anybody.”

A history of support

Syria has been Russia’s top ally in the Middle East since Soviet times, when it was led by the incumbent’s father, Hafez Assad. The Kremlin saw it as a bulwark for countering U.S. influence in the region and heavily armed Syria against Israel.

After Assad succeeded his father in 2000, Russia sought to boost ties by agreeing to annul 73 percent of Syria’s Soviet-era debt. In the mid-2000s, Putin said Russia would re-establish its place in the Mideast via “the Syria route.”

Syria’s port of Tartus is now the only naval base Russia has outside the former Soviet Union. A Russian navy squadron made a call there this month in what was seen by many as a show of support for Assad.

For decades, Syria has been a major customer for Russian arms industries, buying billions of dollars’ worth of combat jets, missiles, tanks and other heavy weapons. And unlike some nations, such as Venezuela, which obtained Russian weapons on Kremlin loans, Assad’s regime paid cash.

The respected newspaper Kommersant reported this week that Syria has ordered 36 Yak-130 combat jets worth $550 million. The deal, which officials wouldn’t confirm or deny, may signal preparations for even bigger purchases of combat planes.

Korotchenko said Syria needs the jets to train its pilots to fly the advanced MiG-29M or MiG-35 fighter jets it wants to purchase: “It’s a precursor of future deals.”

Korotchenko said Syria’s importance as a leading importer of Russian weapons in the region grew after the loss of the lucrative Iraqi and Libyan markets.

Earlier this month, a Syria-bound Russian ship allegedly carrying tons of munitions was stopped by officials in EU member Cyprus, who said it was violating an arms embargo. The captain promised to head to Turkey but then made a dash to Syria.

The most powerful Russian weapon reportedly delivered to Syria is the Bastion anti-ship missile complex intended to protect its coast. The Bastion is armed with supersonic Yakhont cruise missiles that can sink any warship at a range of 186 miles and are extremely difficult to intercept, providing a strong deterrent against any attack from the sea.