METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE synthesis
- Product Name:METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE
- CAS Number:78962-39-7
- Molecular formula:C13H24O11
- Molecular Weight:356.32
![α-D-Mannopyranoside, methyl 6-O-[2-O-acetyl-3,4,6-tris-O-(phenylmethyl)-α-D-mannopyranosyl]-2,3,4-tris-O-(phenylmethyl)-](/CAS/20210305/GIF/195875-44-6.gif)
195875-44-6
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Yield:78962-39-7 77%
Reaction Conditions:
Stage #1: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranosidewith sodium methylate in methanol at 20; for 24 h;Inert atmosphere;
Stage #2: with palladium 10% on activated carbon;hydrogen;acetic acid in methanol at 20; for 72 h;
Steps:
Methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside (1) (Sandstr?m et al., 2004).
Compound 30 (289 mg, 0.308 mmol) was dissolved in MeOH (10 mL). Then NaOMe (9 mg, 0.2mmol) in MeOH (0.5 mL) was added and the reaction mixture was stirred at rt under nitrogen for24 h. Then AcOH (70 μL, 1.2 mmol) and Pd (10% on C) (160 mg, 0.15 mmol) was added to andthe reaction mixture was stirred at rt under hydrogen for 72 h. Then, the reaction mixture wasfiltered through celite and rinsed with MeOH. The combined filtrate was evaporated under reducedpressure giving 138 mg of crude product. The crude product was separated by flash columnchromatography with solvent system DCM:MeOH 3:1 giving pure compound 1 (84 mg, 77%). TLC(DCM/MeOH 3:1): Rf 0.10; 1H-NMR (500 MHz, D2O): 4.90 (d, J = 1.6 Hz, 1 H, H-1’), 4.74 (d, J =1.6 Hz, 1 H, H-1), 3.96-3.99 (m, 2 H, H-2’), 3.93-3.94 (m, 1 H, H-2), 3.89 (dd, J = 2.0 Hz and 12.0Hz, 1 H), 3.84 (dd, J = 3.5 Hz and 9.4 Hz, 1 H), 3.68-3.77 (m, 6 H, H-3), 3.65 (at, J = 9.5 Hz, 1 H),3.40 (s, 3 H, OMe). 13C-NMR (125 MHz, D2O): 101.6, 100.1, 73.3, 71.4, 71.3, 71.2, 70.6, 70.5,67.3, 67.1, 66.2, 61.5, 55.4
References:
Norberg, Oscar;Wu, Bin;Thota, Niranjan;Ge, Jian-Tao;Fauquet, Germain;Saur, Ann-Kathrin;Aastrup, Teodor;Dong, Hai;Yan, Mingdi;Ramstr?m, Olof [Carbohydrate Research,2017,vol. 452,p. 35 - 42] Location in patent:supporting information
13242-53-0
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