So there's 2 topics here, both about field values.
1. What does comma mean?
2. What does dquote mean?
If there is a comma present, and it's not within a DQUOTE pair, then that's the delimiter between field-values.
So that means ...
Example 1:
X-Foo: apple, banana, pear
Is a field of name "X-Foo", with 3 values:
1. apple
2. banana
3. pear
This can also be represented across multiple headers of the same name.
Example 2:
X-Foo: apple
X-Foo: banana
X-Foo: pear
Those 2 examples are equivalent field definitions.
Those 3 values, as they are written, are considered "token" field values per spec.
You can have a field value of either:
1. a token
2. quoted-string
3. comment
The rules for "token" are ...
token = 1*tchar
tchar = "!" / "#" / "$" / "%" / "&" / "'" / "*"
/ "+" / "-" / "." / "^" / "_" / "`" / "|" / "~"
/ DIGIT / ALPHA
; any VCHAR, except delimiters
Also, it notes that delimiters are (DQUOTE and "(),/:;<=>?@[\]{}")
The rules for "quoted-string" are ...
quoted-string = DQUOTE *( qdtext / quoted-pair ) DQUOTE
qdtext = HTAB / SP /%x21 / %x23-5B / %x5D-7E / obs-text
obs-text = %x80-FF
If we take these rules and apply it to your stated example strings ...
Your Example 1:
If-Match: "ab35ef1bc78", "5be73a9c523"
This is a field of name "If-Match", with 2 quoted-string values.
1. ab35ef1bc78
2. 5be73a9c523
Your Example 2:
If-Match: W/"ab35ef1bc78", W/"5be73a9c523"
This is a field of name "If-Match".
It has 2 values, both of which are in violation of the spec.
Why?
This is started to be parsed as a token, as it doesn't start with DQUOTE.
This field-value has 3 forbidden delimiter characters, the "/" is invalid, and so are the DQUOTE characters.
This example doesn't fit the definition for quoted-string either, as it doesn't start with DQUOTE.
If your example was ...
If-Match: "W/ab35ef1bc78", "W/5be73a9c523"
Then you would satisfy the quoted-string rules. (as the "/" is %x2F and within the allowed qdtext definition).
And the parsed definition would be ..
Field with name "If-Match", with a value list
1. W/ab35ef1bc78
2. W/5be73a9c523