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男の人は息子さんほど大きいケーキを持っていません。

女の人は息子さんほどたくさんのジュースを持っていません。

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男の人は息子さんほど大きいケーキを持っていません。

The man's cake is not as big as his son's.

息子さんほど大きいケーキ in this context means "the bigness of the son's cake".

女の人は息子さんほどたくさんのジュースを持っていません。

The woman doesn't have a lot of juice like her son does.

息子さんほどたくさんのジュース in this context means "the son's large amount of juice".

The ほど in these sentences indicate the degree/amount/extent of what comes after it. The Jisho.org entry has a suitable example sentence:

スージーほど上手にピアノをひけるとよいのだが。

I wish I could play piano as well as Susie.

In each sentence a comparison is made between two people, and the one that precedes ほど is the person being compared to.

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