Devices and methods are provided for sterile transfer of flowable material between a syringe and one or more flowable material receptacles or between a pair of receptacles. A syringe assembly may include a tip enclosure having a flexible shroud surrounding a syringe tip, with a shroud membrane associated with the distal end of the shroud to enclose the syringe tip. The shroud is deformable to move the tip toward the shroud membrane, which may be traversed by the tip to expose the tip for material transfers. A rigid connector may be positioned at the distal end of the shroud to securely connect the syringe assembly to a receptacle. The plunger and piston of the syringe assembly may include membranes to allow material transfer at the proximal end of the syringe assembly. An adaptor may also be provided for sterilely connecting a receptacle to a syringe or to another receptacle.
