Synthesis of Hydroxylated Analogues of α‐Galactosyl Ceramide (KRN7000) with Varying Stereochemistry

Abstract

The synthesis of analogues of α‐galactosyl ceramide (KRN7000) with an additional hydroxy group in the phytosphingosine chains and with varying stereochemistry is described. Careful selection of glucose, galactose, mannose, and talose hexopyranoses allowed us to control the stereochemistry of some of the hydroxy groups in the sphingosine chain to give some interesting hydroxylated KRN7000 analogues.

Synthesis and Bioassay of Neurogenically Potent Gangliosides DSG-A, Hp-s1 and Their Analogues

“…We intended to design the analogue with C5 hydroxyl group, which may enhance the interaction with the receptors to produce higher potency of analogue. For this purpose, synthesis of 5-substituted ceramide acceptors 6a, 6b was carried out, 24 which subsequently gave intermediate products 7a and 7b after coupling with donor 4 using TMSOTf as a promotor followed by removal of O-6 acetyl group using sodium methoxide (Scheme 2).…”

H2SO4-Silica: An Efficient Promoter for Selective Removal of Benzylidene and Isopropylidene Groups in the Presence ofp-Methoxybenzyl Group

“…To a solution of known p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside [31] (560 mg, 1 mmol) in dry DMF (5 mL), NaH (100 mg, 50% in mineral oil) was added followed by PMBCl (1.5 mmol) and the mixture was allowed to stir at rt for 2 h. Then MeOH (1 mL) was added to quench excess NaH and the solvents were evaporated. The residue was dissolved in CH 2 Cl 2 (20 mL) and washed successively with water (20 mL) and brine (20 mL).…”

Synthesis of Chrysogeside B from Halotolerant Fungus Penicillium and Its Antimicrobial Activities Evaluation

“…There are generally two strategies for synthesis of cerebrosides. The first one contains the process in which an azide group is incorporated before generation of 1-glycosylated-2-azidosphingosine from the substituted glycosidic ligand, and then azide group is reduced to generates the amine for condensation with α-hydroxyl-β,γ-unsaturated acid 9 10 11 12 . The second approach, used by Wu 13 , Huang 14 , Lim 15 , and Thakur 16 , doesn’t rely on azide group to introduce amino group in sphingosine fragment synthesis.…”