According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.
Application of 61881-19-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 61881-19-4 as follows.
A solution of isomaltose (100 mg, 0.292 mmol) in dry pyridine(2.0 mL) was treated with acetic anhydride (0.8 mL) and 4-(N,Ndimethylamino)pyridine (5 mg) at 0 C and after 20 h at ambienttemperature, excessive reagent was destroyed by adding dry MeOH(2.0 mL) at 0 C. After 10 min the solvent was coevaporated withtoluene (3×) and the residual oil was purified by chromatography(n-hexane/EtOAc 1:1 ? 1:2) affording an alpha/beta-mixture (1:1) ofperacetylated isomaltose (198 mg, quantitative yield). The residue(101 mg, 0.149 mmol)was dissolved in dry DMF (2.0 mL) and treatedwith hydrazine acetate (27 mg, 0.298 mmol) at 40 C for 2 h underAr. The mixture was diluted with EtOAc, washed with cold brineand the organic layer was dried (MgSO4) and filtered. Concentrationof the filtrate provided a crude product, which was purifiedby chromatography (n-hexane/EtOAc 1:2) to obtain an alpha/beta-mixture (1:0.3) of the hemiacetal (85 mg, 90%): 1H NMR (CDCl3): delta5.53 (dd, 1H, J3alpha,2alpha 10.1, J3alpha,4alpha 9.4 Hz, H-3alpha), 5.46 (app t, 1H, J3?beta,2?beta ~ J3?beta,4?beta9.8 Hz, H-3?beta), 5.45 (app t, 1H, J3?alpha,2?alpha ~ J3?alpha,4?alpha 9.8 Hz, H-3?alpha), 5.40(app t, 1H, J1alpha,2alpha ~ J1alpha,OH 3.5 Hz, H-1alpha), 5.23 (app t, 1H, J3beta,2beta ~ J3beta,4betaHz, H-3beta), 5.14 (d, 1H, J1?beta,2?beta 3.8 Hz, H-1?beta), 5.13 (d, 1H, J1?alpha,2?alpha3.8 Hz, H-1?alpha), 5.02-4.97 (m, 3H, H-4?alpha, H-4beta, H-4alpha), 4.94 (dd, 1H,J4alpha,5alpha 10.3 Hz, H-4alpha), 4.85-4.78 (m, 4H, H-2alpha, H-2?alpha, H-2beta, H-2?beta),4.73 (app t, 1H, J 8.0 Hz, H-1beta), 4.24 (ddd, 1H, J5alpha,6aalpha 6.5, J5alpha,6balpha2.5 Hz, H-5alpha), 4.21-4.05 (m, 7H, H-5?alpha, H-5?beta, H-6?aalpha, H-6?abeta,H-6?balpha, H-6?bbeta, OHbeta), 4.02-3.99 (m, 1H, OHalpha), 3.74-3.57 (m,5H, H-5beta, H-6aalpha, H-6abeta, H-6balpha, H-6bbeta), 2.10 to 2.00 (10 s, 14×COCH3); ESI-TOF HRMS: m/z = 659.1794; calcd for C26H36O18Na+:659.1798.The residue (70 mg, 0.110 mmol) was dissolved in dry CH2Cl2(1.8 mL) and dry acetone (1.0 mL). Potassium carbonate (30 mg,0.220 mmol) and 2,2,2-trifluoro-N-phenylacetimidoyl chloride (35 muL,0.220 mmol) were added successively under Ar. The suspension wasstirred for 12 h at rt, then filtered through a pad of Celite, rinsedwith CH2Cl2 and the filtrate was concentrated. Swift chromatographicpurification (n-hexane/EtOAc 1:1) provided 17 (80mg, 90%)which was directly used for the subsequent glycosylation reaction.1H NMR spectra of 17 (CDCl3) displayed broad signalscorresponding to a 2.5:1 mixture; 13C NMR (125 MHz, CDCl3, selecteddata): delta 169.8-168.9 (C = O, Ac), 142.8, 128.9, 128.8 124.7 and119.4 (arom. C), 96.0 (C-1, C-1?), 66.4 and 66.2 (C-6), 61.7 (C-6?), 20.6-20.4 (CH3CO).
According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.
Reference:
Article; Pokorny, Barbara; Kosma, Paul; Carbohydrate Research; vol. 422; (2016); p. 5 – 12;,
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