"Jack Ma is very astute and he noticed that Facebook tripped over its initial public offering and doesn't want to do the same thing, so better to low ball it a bit and let it rise as it goes into the market than let the public investors feel like they have been short changed and had paid too much," Roger Kay, president at Endpoint Technologies told CNBC on Monday.
The Chinese e-commerce behemoth on Friday said it expects to price its IPO between $60 and $66 per share to raise as much as $24.3 billion - making it the largest U.S. public offering in history.
At $66 a piece, Alibaba would be valued at $163 billion - below analysts' expectations for a valuation of more than $200 billion.
Facebook, the world's largest technology IPO to date, raised $16.01 billion in its May 2012 debut in New York. It had a market capitalization of $81.25 billion, according to Associated Press.
Shares of the social networking giant lost one-third of their value within two months of their debut.
However, some analysts believe Alibaba may eventually price above the initial range if investor demand is stronger than anticipated.
Alibaba is due to kick off its roadshow in New York on Monday and is expected to hold 100 meetings in less than two weeks.
Under the proposed timeline, Alibaba shares will be priced on Sept. 18, and will begin trading on the New York Stock Exchange the following day, under the ticker symbol BABA.
"The valuation here is really below what we had expected. We are expecting [a valuation of around] $200 billion, which would translate into $90-100 per share," said Henry Guo, senior research analyst at JG Capital.
Guo is optimistic that Alibaba shares will avoid a Facebook-like debut flop and perform well on their first day of trade.
"When I talk to investors in the U.S., the overall view is very positive. I'm expecting a very good first day of trade," he said.
Not everyone's sold on Alibaba's story, though.
Jeff Dorr, equity analyst at J Capital Research says with Alibaba's 80 percent market share in online retail sales in China, growth prospects are limited.
Dorr added that expansion into the U.S. will prove challenging for the e-commerce giant.
"Competition is a bit stiffer with Amazon and eBay heavily entrenched. I expect Alibaba will have a more difficult time getting into the U.S. market," he said.
Difficulty in valuing the highly complex company is also deterring some investors.
Alibaba's business involves several moving parts including business-to-business online web portals, online retail and payment services, a shopping search engine and data-centric cloud computing services.
"It's a very interesting company, it really owns the e-commerce space in China, but then saying what it's really worth, is a difficult one," Sam Le Cornu, senior portfolio manager for Asia listed equities at Macquarie Funds Group (ASX: MQG-AU).
"There's a lot of press on this deal [but] this is one we're probably going to pass on," he added.