Bangladesh face a tough battle to save the series-deciding second and final Test against the West Indies despite opener Tamim Iqbal's bold 82 not out on Tuesday.
The hosts, chasing an improbable victory target of 508, were 164-3 in their second innings at stumps on the penultimate day of the match in Dhaka. Skipper Mushfiqur Rahim was unbeaten on 33.
Darren Bravo earlier smashed five sixes and 12 fours on his way to a 297-ball 195, before the West Indies, leading by 124 runs on the first innings, declared their second innings closed on 383-5.
The opening Test of the two-match series ended in a draw in Chittagong.
Bangladesh lost opener Imrul Kayes (nine), Shahriar Nafees (18) and Raqibul Hasan (17), but left-handed Tamim continued to defy the West Indies' attack, having so far cracked one six and eight fours.
Fast bowler Fidel Edwards, who jolted Bangladesh with five quick wickets in the first innings, struck in his second over when he had Kayes caught by Kirk Edwards at first slip.
Seamer Darren Sammy held a return catch to dismiss Nafees (18) in the last over of the afternoon session before off-spinner Marlon Samuels removed Raqibul.
Tamim, dropped at point on 12 by Samuels off Fidel Edwards, made the most of the chance and played some attractive strokes in his 149-ball knock.
Bravo fell in the afternoon session, top-edging a delivery from debutant left-arm spinner Suhrawadi Shuvo to wicket-keeper Rahim.
He had hit a six off the previous ball before going for another big shot in a bid to complete his double-century.
The West Indies added 176 runs to their overnight total of 207-3 before declaring after Bravo's dismissal.
Bravo, who completed his maiden Test hundred off the last ball on Monday, reached the 150-mark in the last over of the morning session with a four off Shuvo.
West Indies: 355 & 383/5 declared
Bangladesh 1st innings: 231
Bangladesh 2nd innings 164-3 (Tamim Iqbal 82, Mushfiqur Rahim 33)