Preciso que vc me responda algumas perguntas: Qual versão do iTunes e o do iTunes Sync você está usando? Qual versão do Windows?

Algo que vc pode fazer logo é reiniciar o computador e configurar o iTunes Sync novamente. Também vale tentar desinstalar o programa e reinstalá-lo.

Qualquer coisa vc pode me adicionar no Facebook e podemos conversar por lá: facebook.com/eduardobuarque

Abraço.

See the end of this message for details on invoking
just-in-time (JIT) debugging instead of this dialog box.

************** Exception Text **************
System.InvalidCastException: Unable to cast COM object of type ‘iTunesLib.iTunesAppClass’ to interface type ‘iTunesLib.IiTunes’. This operation failed because the QueryInterface call on the COM component for the interface with IID ‘{9DD6680B-3EDC-40DB-A771-E6FE4832E34A}’ failed due to the following error: Não há suporte para esta interface (Exception from HRESULT: 0×80004002 (E_NOINTERFACE)).
at iTunesLib.iTunesAppClass.get_LibrarySource()
at e.a(iTunesApp A_0, Boolean A_1)
at j.b()
at j.d(Object A_0, EventArgs A_1)
at System.Windows.Forms.Form.OnLoad(EventArgs e)
at System.Windows.Forms.Form.OnCreateControl()
at System.Windows.Forms.Control.CreateControl(Boolean fIgnoreVisible)
at System.Windows.Forms.Control.CreateControl()
at System.Windows.Forms.Control.WmShowWindow(Message& m)
at System.Windows.Forms.Control.WndProc(Message& m)
at System.Windows.Forms.ScrollableControl.WndProc(Message& m)
at System.Windows.Forms.ContainerControl.WndProc(Message& m)
at System.Windows.Forms.Form.WmShowWindow(Message& m)
at System.Windows.Forms.Form.WndProc(Message& m)
at System.Windows.Forms.Control.ControlNativeWindow.OnMessage(Message& m)
at System.Windows.Forms.Control.ControlNativeWindow.WndProc(Message& m)
at System.Windows.Forms.NativeWindow.Callback(IntPtr hWnd, Int32 msg, IntPtr wparam, IntPtr lparam)

************** Loaded Assemblies **************
mscorlib
Assembly Version: 2.0.0.0
Win32 Version: 2.0.50727.3082 (QFE.050727-3000)
CodeBase: file:///c:/WINDOWS/Microsoft.NET/Framework/v2.0.50727/mscorlib.dll
—————————————-
iTunes Sync
Assembly Version: 1.5.1.0
Win32 Version: 1.5.1.0
CodeBase: file:///C:/Arquivos%20de%20programas/iTunes%20Sync/iTunes%20Sync.exe
—————————————-
System.Windows.Forms
Assembly Version: 2.0.0.0
Win32 Version: 2.0.50727.3053 (netfxsp.050727-3000)
CodeBase: file:///C:/WINDOWS/assembly/GAC_MSIL/System.Windows.Forms/2.0.0.0__b77a5c561934e089/System.Windows.Forms.dll
—————————————-
System
Assembly Version: 2.0.0.0
Win32 Version: 2.0.50727.3053 (netfxsp.050727-3000)
CodeBase: file:///C:/WINDOWS/assembly/GAC_MSIL/System/2.0.0.0__b77a5c561934e089/System.dll
—————————————-
System.Drawing
Assembly Version: 2.0.0.0
Win32 Version: 2.0.50727.3053 (netfxsp.050727-3000)
CodeBase: file:///C:/WINDOWS/assembly/GAC_MSIL/System.Drawing/2.0.0.0__b03f5f7f11d50a3a/System.Drawing.dll
—————————————-
Interop.iTunesLib
Assembly Version: 1.11.0.0
Win32 Version: 1.11.0.0
CodeBase: file:///C:/Arquivos%20de%20programas/iTunes%20Sync/Interop.iTunesLib.DLL
—————————————-
System.Xml
Assembly Version: 2.0.0.0
Win32 Version: 2.0.50727.3082 (QFE.050727-3000)
CodeBase: file:///C:/WINDOWS/assembly/GAC_MSIL/System.Xml/2.0.0.0__b77a5c561934e089/System.Xml.dll
—————————————-

************** JIT Debugging **************
To enable just-in-time (JIT) debugging, the .config file for this
application or computer (machine.config) must have the
jitDebugging value set in the system.windows.forms section.
The application must also be compiled with debugging
enabled.

For example:

When JIT debugging is enabled, any unhandled exception
will be sent to the JIT debugger registered on the computer
rather than be handled by this dialog box.

Um abraço.

Se vc consegue usá-lo como pendrive, só é seguir o passo-a-passo mostrado aqui.

Vc pode tb ir na página do desenvolvedor do programa: http://www.binaryfortress.com/itunes-sync/

lá ele lista uma série de marcas e modelos de palyers compatíveis com o programa.