Here's a solution using the titleps package and its extramarks option:
\documentclass{book}
\usepackage[headheight=30pt]{geometry}
\usepackage[T1]{fontenc}
\usepackage{titlesec}
\usepackage[extramarks]{titleps}
\usepackage{lipsum}
\setcounter{secnumdepth}{4}
\settitlemarks*{chapter,section,subsection,subsubsection,paragraph}
\newpagestyle{main}[\small\sffamily]{
\sethead{%
\parbox{\textwidth}{%
\thechapter~\chaptertitle\space%
\ifnum\value{section}>0 \guillemotright\ \else\fi%
\thesection~\sectiontitle\space%
\ifnum\value{subsection}>0 \guillemotright\ \else\fi%
\thesubsection~\subsectiontitle\space%
\ifnum\value{subsubsection}>0 \guillemotright\ \else\fi%
\thesubsubsection~\subsubsectiontitle\space
\ifnum\value{paragraph}>0 \guillemotright\ \else\fi%
\theparagraph~\paragraphtitle%
}
}{}{}}
\pagestyle{main}
\makeatletter
\let\ps@plain\ps@main
\makeatother
\newcommand\subsectionbreak{\clearpage}
\begin{document}
\chapter{Test Chapter One}
\section{Test Section One One}
\lipsum[1-5]
\subsection{Test Subsection One One One}
\lipsum[1-5]
\subsection{Test Subsection One One Two}
\lipsum[1-5]
\subsubsection{Test Subsection One One Two One}
\lipsum[1-5]
\paragraph{Test Paragraph One One Two One One}
\lipsum[1-5]
\end{document}
Some images taken from some of the pages to see the headers:

and

As a personal note, I don't think it's a good idea to use such longer headers.