143774-07-6

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 136882-36-5 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 

Downstream Products

• 950515-42-1 C₄₀H₄₁NO₈SSi 
• 395072-15-8 p-methoxyphenyl 3,4-di-O-benzoyl-6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 395072-13-6 phenyl 6-O-acetyl-3,4-di-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 400020-10-2 OCHSC₆H₅CHNCOCOC₆H₄CHCH(OCOC₆H₅)2CHCH₂OH 

Relevant academic research and scientific papers

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.

De-O-benzylation of sterically hindered benzyl ethers

Sterically hindered benzyl ethers that cannot be removed by hydrogenolysis with a variety of catalysts are removed readily by the reaction with N-bromo-succinimide and light in the presence of aqueous calcium carbonate, a reaction developed by Binkley and Hehemann. It was found that these conditions are compatible with the presence of phthalimides and glycosyl sulfides and fluorides, in addition to the groups previously shown to be inert.

A synthetic pentasaccharide with GTPase activity.

The design, synthesis, and preliminary evaluation of the first example of synthetic pentasaccharide (1) that shows marked rate enhancement and specificity for the hydrolysis of GTP to GDP and orthophosphate (OP) are reported. At the concentration ratios of GTP/1 = 3.6 and GTP/Mg(2+) = 1 (pH 7.1, 50 degrees C), a rate enhancement of about 500-fold was obtained.[reaction: see text]