ChemicalBook CAS DataBase List BENZYL ALPHA-D-GLUCOPYRANOSIDE

BENZYL ALPHA-D-GLUCOPYRANOSIDE synthesis

8synthesis methods

Product Name:BENZYL ALPHA-D-GLUCOPYRANOSIDE
CAS Number:25320-99-4
Molecular formula:C13H18O6
Molecular Weight:270.28

2280-44-6
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100-51-6 Synthesis

100-51-6
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25320-99-4
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$45.00/100mg

Yield:25320-99-4 68%

Reaction Conditions:

with toluene-4-sulfonic acid at 75 - 90; for 18 h;

Steps:

Synthesis of 1-O-Benzyl-D-glucopyranoside (14)

To a mixture of D-glucose (5 g, 27.8 mmol) and p-TsOH(0.53 g, 2.78 mmol) was added BnOH (13.6 ml, 130.6 mmol). The mixture was then heated to 90°C and stirred until D-glucose dissolved to give a slightly yellow solution. The reaction mixture was then stirred at 75°C for 18 h and then cooled to rt. Purification of the crude product by column chromatography using hexane-EtOAc(2:1) followed by DCM-EtOH (8:16:1) as the eluent furnished the pure compound 14 (yield=68%). 1HNMR (500 MHz, CD3OD) δ 7.36 - 7.19 (m, 5H), 4.88 - 4.86 (m, 1H), 4.63 - 4.58 (m, 1H), 4.33 - 4.28 (m,1H), 3.86 - 3.83 (m, 1H), 3.66 - 3.64 (m, 1H), 3.33 - 3.20 (m, 4H). 13C NMR (125 MHz, CD3OD) δ139.03,129.28, 129.22, 128.66, 99.24, 75.08, 73.86, 73.55, 71.81, 70.20, 62.63 HRMS (ESI) calcd for C13H18O6Na(M+Na)+: 293.1001, found 293.1010.

References:

Susanto, Woen;Kong, Kah-Hoe;Hua, Kuo-Feng;Wu, Shih-Hsiung;Lam, Yulin [Tetrahedron Letters,2019,vol. 60,# 3,p. 288 - 291] Location in patent:supporting information