That is a pretty good compression number - on the order of 22 atmospheres - especially for a turbo. Typically a turbo has a lower "nominal" compression ratio since under load it gets a pressurized slug of air.

If that is truly your compression, the only issues I can attribute your problem to are the glow plugs are not up to snuff, and your injectors are likely a little leaky. This, in combination with the cold freaking air being sucked in and circulated around is quenching the combustion attempt before it gets going. The first shot has a presumably dry set of glow plugs reaching a relatively high temperature for the first shot of fuel. If that fuel arrives imitating mucus from a sneeze instead of a fine spray, the combustion is not going to be complete. But, if the engine speed is increased while you continue to crank the starter, the engine will fire as it climbs up the thermodynamic capability curve with higher speed. IF you stop before the engine is running, the glow plugs will be wet, and they won't really be hot when the glow cycle is over - they get cooled as the wet fuel evaporates. The combination of cool plugs and cold air being sucked in conspires to make starting difficult or impossible the second time around.

When the glow plugs and injectors are not up to snuff, on a really cold day you are going to wear down your battery and weaken your starter. Which makes things just that much worse.

Jim

__________________
Own:
1986 Euro 190E 2.3-16 (291,000 miles),
1998 E300D TurboDiesel, 231,000 miles -purchased with 45,000,
1988 300E 5-speed 252,000 miles,
1983 240D 4-speed, purchased w/136,000, now with 222,000 miles.
2009 ML320CDI Bluetec, 89,000 miles

Owned:
1971 220D (250,000 miles plus, sold to father-in-law),
1975 240D (245,000 miles - died of body rot),
1991 350SD (176,560 miles, weakest Benz I have owned),
1999 C230 Sport (45,400 miles),
1982 240D (321,000 miles, put to sleep)