Chanderpaul, a veteran of 148 Tests, gave ample indications of the challenge he would pose to Indian bowlers. He remained unconquered on a nicely made 91 (11x4, 2x6), as the visitors raced to 333/4 at the Jadavpur University ground.
Giving Chanderpaul company at the stumps was Narsingh Deonarine (83; 10x4, 3x6), with the duo having added 170 runs for the fifth wicket on a low and slow surface, which eased as the day progressed.
Winning the toss, the visitors rode on four individual half centuries and two hundred plus stands to be on track for a massive total, and benefitting substantially from a listless bowling effort by their rivals.
Kieran Powell (64; 121 b, 12x4) and Darren Bravo (61; 79 b, 12x4) put on 112 runs for the second wicket, that offset the early loss of the destructive Chris Gayle (18) after play started an hour late due to a soggy outfield.
Gayle, arguably one of the most destructive batsmen of the current generation, began aggressively picking up three boundaries with firm pushes and a straight drive, but did not last long.
The Jamaican saw his middle stump uprooted, deceived by a low offering from pacer Imtiaz Ahmed with the team score on 33. Bravo, coming back after an eye surgery, played some scintillating shots,though he was lucky to be dropped on 18.
Bravo's 116-minute stay at the crease came to an end when he played on to the stumps an R.P. Singh delivery. Bravo's dismissal saw a mini collapse, as West Indies lost two more wickets with the addition of only 18 runs.
Powell was foxed by a turning delivery from offie Arish Alam and saw his off stump knocked out. Marlon Samuels (12) went cheaply as he inside-edged an Ahmed delivery and was taken behind the stumps.
Chanderpaul, 39, played cautiously initially, trying to size up the conditions on a ground hosting an international side for the first time.
However, he opened up in the post-tea session, coming up with some sublime strokes that gave much joy to the spectators watching the game from beside bamboo barricades put up to control the crowd.