Luke Andrew Lazarus, 23, was sentenced on Friday to a maximum jail term of five years.

District Court Judge Sarah Huggett described the attack as the "spontaneous and opportunistic" actions of a young man who felt a sense of "power and entitlement" by virtue of his family's connection to the Soho club.

Dozens of family members and friends who supported Lazarus in the Downing Centre District Court on Friday gasped and sobbed as Judge Huggett handed down her sentence.

A string of prominent people, including Waverley mayor Sally Betts, the honorary secretary of the Honorary Consulate-General of Greece in Brisbane, Tsambico K Athanasas and South Sydney Rabbitohs rugby league club chairman Nick Pappas had provided references for Lazarus, unanimously declaring their shock at his conviction and vying for his good character.

Ms Betts urged the court not to jail Lazarus while the parish priest at the Greek Orthodox Christian Church of St George, Rose Bay, Father Gerasimos Koutsouras said: "The possibility of imprisonment is completely undeserved for this promising young man."

But the judge said a full time jail sentence was the only option as she was satisfied Lazarus didn't "care one way or the other" as to whether the young woman was consenting.

During the hour-long sentencing hearing, his father, Andrew Lazarus, hid his face behind his hands while, in the dock, his son looked down, repeatedly rubbing his face.

Judge Huggett ordered that Lazarus be referred to mental health professionals from Justice Health while in custody.

Lazarus, a former Cranbrook student, worked in marketing for beverage giant Lion but resigned upon his conviction by a jury last month.

He claimed the 18-year-old was a willing participant because she didn't physically resist, scream or say no.

The court heard that, in the early hours of May 12, 2013, the victim went to the Soho club on Victoria Street, Potts Point, with a friend after spending the previous hours drinking at her sister's Sydney home and the nearby World bar. It was her first visit to Kings Cross.

Lazarus, who worked casually for his father, the part owner of Soho and the Eastern Hotel at Bondi Junction, approached the woman on the dance floor and told her he owned the club and invited her to the VIP area.

He led her by the hand to an exit door that opened on to the alley. The couple kissed but she said she wanted to return to her friend.

As she went to leave, Lazarus pulled her stockings and skirt down and said in aggressive tone, "Put your f---ing hands on the wall."

He then told her to go down on her hands and knees and to "arch your back".

The victim told the court that she was alone in a dark alley and frightened.

As he anally raped her, she said "I'm a virgin."

After about 10 minutes, he gave her his mobile phone, which had a list of women's names. He told her to add hers to the bottom of the list.

In cross-examination Lazarus' barrister, Ian Lloyd, QC, suggested the victim's attitude towards the sexual encounter changed after seeing the list because she felt used or like a trophy. She denied this was the case.

In a text message to a friend the afternoon after the attack, Lazarus said: "I honestly have zero recollection of calling you ... Was a sick night – took a chick's virginity."

His friend replied: "bahahahaha nice popping does cherries ... "

Lazarus replied: "... it's a pretty gross story tell ya later".

The note section of his phone also contained a list of female names, with his victim's name appearing at the end of the list.

In a victim impact statement read to the court during sentencing submissions, the victim said she spent days sitting in a bath after the attack and, in the two years since, had cried until she "couldn't breathe, crying until I physically couldn't any more".

"I'll never be who I was. I had to rebuild myself with what I had left," she said in the statement.

"A part of me died that day, the part that trusted others."

Judge Huggett said she was satisfied the victim was scared and intimidated by the power imbalance between Lazarus and her.

"She had the right to go to Kings Cross, to be intoxicated, to kiss a man. She also had the right to say she wanted to return to her friend. The offender ignored that."

In his sentencing hearing on Thursday, Lazarus cried as he told the court he once had "the world at my feet" and "I could have been a CEO."

He said media coverage of the trial and conviction had caused his privileged life to come crashing down around him. He has been vilified on social media and has been prescribed antidepressant and sedative medication.

"My life, at least in Australia, has been completely destroyed and now I have to live the rest of my life knowing every single person in Australia, or at least Sydney, knows I have been convicted of a sex offence," he said.

He said he was "shattered, horrified and sickened" after hearing the woman's victim impact statement.

Judge Huggett accepted Lazarus' offending occurred in the context of a recent break-up with his American girlfriend, who was not of Greek heritage, sparked by his parents' ultimatum that he had to choose between her and his family.

He had experienced bullying at school, in part due to his short stature, and he revelled in the power and entitlement he enjoyed as the club owner's son.

He has also expressed some remorse, claiming he would have "never deliberately hurt her".

But neither the media coverage nor his mental health issues reduced his "moral culpability", Judge Huggett said.

However, she did acknowledge jail would be more onerous for him than "ordinary" inmates.

In a character reference tendered to the court Lazarus's father Andrew said there has been a "major backlash" against the Soho nightclub since the Herald reported his son's conviction on March 8.

He said there has been "a significant decline in patronage" and after 19 years he is going to sell out.

Mr Lazarus said the family had hoped to keep his eldest son's conviction under wraps. "It was our intention and hope that the incident could remain quiet to > protect Luke's good reputation," he said.

"I didn't even inform my mother and sisters as I was acutely aware of  how painful this would be for Luke and all his family and friends."

"Luke had a very bright future and he often discussed his aspirations, commitment and belief that he one day would be CEO of [food and beverage multinational company] Lion. None of this is now possible as a registered sex offender."

Mr Lazarus said Luke believes he will need to move overseas and change his name to begin a new life.

The mayor of Waverley Sally Betts urged the sentencing judge to avoid sentencing Lazarus to jail. In a written reference Ms Betts said she has known the Lazarus family for many years and holds them in high esteem. She said she was shocked to learn of his conviction as she knows him as upstanding member of society.

"The conviction is inconsistent with the gentle well mannered and respectful young man that I know."

She said the extended Lazarus and Parras families are deeply embarrassed by media coverage of Luke's conviction. "Luke is suffering greatly as a result of the shame he has bought on his family," she said. "I have no hesitating in supporting the whole Lazarus Parras family including Luke."

The chairman of the South Sydney Rabbitohs rugby league club Dr Nick Pappas said he has known Luke since he was young. He said: "I have always observed him to be respectfull, courteous and obliging young man who has, on my observation, never displayed even a hint of  unlawfulness in his conduct."

Dr Pappas said publication of the conviction had hit the extended family hard. "These are people quite unused to the world of our criminal justice system and I know that all of their friends and acquaintances were in utter disbelief when news of the conviction reached the media," Dr Pappas said.

"Above all, Luke has also expressed to me his continuing concern for the complainant and for the anguish she has undoubtedly experienced."

"There is absolutely no doubt in my mind that the personal torment that Luke has suffered during this period has had a life changing and rehabilitative effect on him and for his reason I say to you with confidence that I believe that he will never re-offend again."

Lazarus will be eligible for parole in March 2018.