Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in the chemo-enzymatic synthesis of Shigella flexneri specific oligosaccharides

A compound of one of the following formulae:

• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e ClAcC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y-All;
• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)eC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y-All;
• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e AcC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y-All;
• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e AcC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y;
• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e ClAcC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y;
• ((E1→2)a′(E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)eC((E1→2)a′(E1→4)a(E1→6)b Cl3AcD)y;
• ((E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e ClAcC((E1→4)a(E1→6b)Cl3AcD)y-All;
• ((E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)eC((E1→4)a(E1→6)b Cl3AcD)y-All;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→4)d′B(E1→4)e AcC((E1→4)a(E1→6)b Cl3AcD)y-All;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e AcC((E1→4)a(E1→6)b Cl3AcD)y;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→3)d(E1→4)d′B(E1→4)e ClAcC((E1→4)a(E1→6)b Cl3AcD)y;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)c(E1→4)c′A(E1→4)d(E1→4)d′B(E1→4)eC((E1→4)a(E1→6)b Cl3AcD)y;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)eClAcC((E1→4)a(E1→6)b Cl3AcD)y-All;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)eC((E1→4)a(E1→6)b Cl3AcD)y-All;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)e AcC((E1→4)a(E1→6)b Cl3AcD)y-All;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)e AcC((E1→4)a(E1→6)b Cl3AcD)y;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)eClAcC((E1→4)a(E1→6)b Cl3AcD)y;
• (E1→4)a(E1→6)bCl3AcD)x(E1→3)cA(E1→3)dB(E1→4)eC((E1→4)a(E1→6)b Cl3AcD)y;
• ABClACC(E1→6)Cl3AcD-All;
• ABC(E1→6)Cl3AcD-All;
• ABClAcC(E1→6)Cl3AcD;
• ABAcC(E1→6)Cl3AcD-All;
• ABAcC(E1→6)Cl3AcD;
• ABC(E1→6)Cl3AcD;
• (E1→3)ABClAcCCl3AcD-All;
• (E1→3)ABCCl3AcD-All;
• (E1→3)ABAcCCl3AcD-All;
• (E1→3)ABAcCCl3AcD;
• (E1→3)ABClAcCCl3AcD;
• (E1→3)ABCCl3AcD;
• (E1→4)ABClAcCCl3AcD-All;
• (E1→4)ABCCl3AcD-All;
• (E1→4)ABAcCCl3AcD-All;
• (E1→4)ABAcCCl3AcD;
• (E1→4)ABClAcCCl3AcD;
• (E1→4)ABCCl3AcD;
• A(E1→4)BClAcCCl3AcD-All;
• A(E1→4)BCCl3AcD-All;
• A(E1→4)BAcCCl3AcD-All;
• A(E1→4)BAcCCl3AcD;
• A(E1→4)BClAcCCl3AcD;
• A(E1→4)BCCl3AcD;
• wherein:
• Cl3Ac is Cl3C—C(O)—;
• ClAc is ClCH2—C(O)—;
• All is allyl;
• x and y are 0 or 1, providing x+y=1;
• A is 2)-α-L-Rhap-(1→;
• B is 2)-α-L-Rhap-(1→;
• C is 3)-α-L-Rhap-(1→;
• D is 3)-α-D-GlcpN-(1→or 3)-β-D-GlcpN-(1→;
• E represents a residue α-D-Glcp-;
• a is 0 or 1;
• a′ is:
• −0 or 1 when a is 1;
• −0 when a is 0;
• e is 0 or 1;
• c′ is 0 or 1;
• d and d′ are 0 or 1, providing d+d′=0 or 1;
• c is at each occurrence independently 0 or 1, providing c+c′=0 or 1;
• b is at each occurrence independently 0 or 1, providing a +b=0 or 1;
• or of one of the following formulae:
• at least one of the TES groups or each TES group being optionally independently replaced by a group chosen from TBS, TIPS, PMB or Nap;
• at least one of the Nap groups or each Nap group being optionally independently replaced by a group chosen from TBS, TIPS or PMB;
• wherein:
• All is allyl;
• Z is CIAc or BrAc;
• Nap is 2-naphtylmethyl;
• TES is triethylsilyl;
• TBS is tert-butyldimethylsilyl;
• TIPS is triisopropylsilyl;
• PMB is para-methoxybenzyl;
• PTFA represents N-phenyltrifluoroacetimidyl;
• TCA represents trichloroacetimidyl.