I will suggest that the Old Testament was written in Hebrew, and Jews may be considered the experts on the Old, and they don’t think the two are compatible.
I can recommend this excercise to you: Take a weekend with a good translator’s Bible and go through Matthew and actually compare the Greek text of “fulfilled prophesy” to the Old Testament Hebrew words that are referenced.
They normally work pretty well in Greek, but not in Hebrew, which shows that “Matthew” wasn’t Jewish, and was trying to convince Greek speakers ignorant of rabbinical training that there was a Old Testament prophesy.
First of all “Jews” are not just one group of opinions, even in Jesus’ day what they understood the Hebrew Scriptures to mean was all over the map and still is.
Hence “experts” by what logic? That they don’t think the two are compatible is hardly a surprise, is it?
But it need not take a weekend to find what I believe you have in mind (I trust you’ll correct me if it isn’t an example), Matt.1:23 quote of Isa. 7:14.
“’almah” was rendered by the LXX as “parthenos” in Greek so those translators thought the Hebrew and Greek worked pretty well together as have translators like Lamsa.
Matthew Levi, a Jew, wrote his account in Hebrew so I rather think he would know what the word “almah” was generally understood to mean.