215102-67-3

Upstream product

• 72333-26-7 allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 
• 114853-29-1 allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 215102-68-4 allyl 2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside 
• 215102-70-8 allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->6)-2-deoxy-3,4-bis(O-p-methylbenzoyl)-2-phthalimido-β-D-glucopyranoside 
• 215102-76-4 allyl 6-O-tert-butyldiphenylsilyl-2-deoxy-3,4-di-O-p-methylbenzoyl-2-phthalimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

β-1,4-Galactosyltransferase-catalyzed synthesis of the branched tetrasaccharide repeating unit of Streptococcus pneumoniae Type 14

A chemoenzymatic approach is described towards the branched tetrasaccharide repeating unit, β-d-Galp-(14)-β-d-Glcp-(16)-[β-d-Galp-(14)]-β-d-GlcpNAc, of Streptococcus pneumoniae type 14 in a form suitable for conjugation. The linear trisaccharide acceptor,

Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide

A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.