N-hexacosanoylphytosphingosine synthesis
- Product Name:N-hexacosanoylphytosphingosine
- CAS Number:182362-51-2
- Molecular formula:C44H89NO4
- Molecular Weight:696.18
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Yield:182362-51-2 100%
Reaction Conditions:
with benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate;N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20; for 168 h;
Steps:
4.8. (2S,3S,4R)-2-Hexacosanoylamido-D-ribo-octadecane-1,3,4-triol
Phytosphingosine 17 (200 mg, 0.63 mmol) and hexacosanoic acid(275 mg, 0.69 mmol) were co-evaporated together with toluene (x 3)and dry DMF (6.5 mL) was added followed by PyBOP (656 mg,1.26 mmol) and DiPEA (0.28 mL, 1.58 mmol). The white suspensionwas stirred at rt for 7 d, at which time the solvent was removed underreduced pressure and the desired product crystallised from EtOAc/MeOH (30 mL, 1:1, v/v). The suspension was spun down in a centrifuge,the filtrate removed and the white solid washed twice with EtOAc/MeOH, before it was dried in vacuo to afford the title triol as a whitesolid (440 mg, 0.63 mmol, quantitative). Rf: 0.60 (15% MeOH/CHCl3,v/v, stained with cerium ammonium molybdate); [α]D25=-2.9(c=1.0, pyridine); IR (film) 3313, 2956, 2917, 2850, 1642, 1543,1471, 1086, 1036, 981, 717, 573 cm-1; 1H NMR (600 MHz, 10%CD3OD in CDCl3) 6.90 (d, JNH,2=8.2 Hz, 1H, NH), 3.99 (dd,JNH,2=8.2 Hz, J1a,2=J1b,2=4.5 Hz, 1H, H-2), 3.71 (dd,J1a,1b=11.4 Hz, J1a,2=4.5 Hz, 1H, H-1a), 3.61 (dd, J1a,1b=11.4 Hz,J1b,2=4.5 Hz, 1H, H-1b), 3.49-3.42 (m, 2H, H-3, H-4), 2.13 (t,Jα,β=7.6 Hz, 2H, CH2-α), 1.56-1.51 (m, 2H, CH2-β), 1.36-1.30 (m,2H, H-5), 1.61-1.56 (m, 1H, H-6a), 1.48-1.44 (m, 1H, H-6b), 1.23-1.81(m, 66H, H-7-H-17, H-γ-H-ω-1), 0.80 (t, J17,18=Jω -1,ω=7.0 Hz, 6H,H-18, H-ω); 13C NMR (150 MHz, 10% CD3OD in CDCl3) δ 174.6 (HNC]O), 75.6 (C-3), 72.4 (C-4), 61.1 (C-1), 51.9 (C-2), 36.5 (C-α), 33.0 (C-6),31.84, 29.64, 29.62, 29.60, 29.57, 29.56, 29.45, 29.30, 29.26, 29.23,22.58 (C-7-C-17, C-γ-C-ω-1), 25.77, 25.72 (C-5, C-β), 13.9 (C-18, C-ω); HRMS(ESI) m/z calcd. for [C44H89NO4+H]+: 696.6864, obsd.:696.6837.
References:
Cheng, Janice M.H.;Chee, Stephanie H.;D?len, Yusuf;Verdoes, Martijn;Timmer, Mattie S.M.;Stocker, Bridget L. [Carbohydrate Research,2019,vol. 486,art. no. 107840]
![(2S,3S,4R)-3,4-Bis[(tert-butyldimethylsilyl)oxy]-2-hexacosanoylamino -4-octadecanol](/CAS/GIF/205371-68-2.gif)
205371-68-2
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