From The Hebrew Alphabet...

The Hebrew Alphabet Letter Shin

The twenty-first letter in many of the Semitic alphabets, including Hebrew, is the letter Shin. Its alternative spellings are also Sin or Sheen. Its sound value is that of a voiceless sibilant or /s/.
.Origins
The origins of the letter Shin go all the way back to the Proto-Sinaitic glyph. The letter Shin may have been based on a hieroglyph for a "sun".

The Phoenician letter sin may have been based on a picture or a pictogram of a tooth.
Hebrew Shin / Sin
The Hebrew Alphabet Letter Shin is a representative of two different phonemes: one is that of an alveolar sibilant as in /s/ and the other like an English palato-alveolar sibilant as can be heard in the English word shoe.
Significance
The letter Shin, in gematria, represents the number 300.

When Shin is used as a prefix, it bears the same meaning as do the relative pronouns "which", "that" and "who" in English. When using Hebrew colloquially, Shin and Kaph together mean "when".

The letter Shin is one of seven letters which is able to receive a tagin, which is a special crown, when it is transcribed in a Sefer Torah.

According to the Book of Judges in the Old Testament of the Bible, the tribe of Ephraim was not able to differentiate between Sin and Shin.
In Judaism
The letter Shin, in Judaism, also stands for the word Shaddai, which is one of the names for God. Due to this fact, a priest or kohen forms the letter Shin by using his hands during the recitation of the Priestly Blessing.

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