Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 86520-63-0 | MDL No. : | MFCD07369652 |
Formula : | C16H20Cl3NO10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IBUZGVQIKARDAF-MBJXGIAVSA-N |
M.W : | 492.69 | Pubchem ID : | 11092215 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With gold(III) chloride; phenylacetylene In dichloromethane at 35 - 39℃; for 0.166667h; Molecular sieve; diastereoselective reaction; | |
20% | With gold(I) chloride In dichloromethane at 20℃; for 3h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With boron trifluoride diethyl etherate; In dichloromethane; at -20℃; for 1h;Inert atmosphere; | Entry 27 Boron trifluoride etherate (25 muL, 0.20 mmol, 0.2 eq.) was added dropwise at -20C under argon to a stirred solution of 2,3,4,6-tetra-O-acetyl-alpha-d-galactopyranosyl trichloroacetimidate (1c) (500 mg, 1.01 mmol, 1 eq.) and <strong>[67853-03-6]methyl 3-hydroxymethylbenzoate</strong> (2d) (503 mg, 3.03 mmol, 3 eq.) in freshly distilled CH2Cl2 (8 mL). After 1 hour, Et3N (0.2 mL) was injected into the reaction mixture. Then, the solvent was evaporated, the residue was purified by silica gel column chromatography (PE:EtOAc, 5:1 to 3:1) to afford (1-methoxycarbonylphen-3-yl)methyl 2,3,4,6-tetra-O-acetyl-beta-d-galactoside (3e) as a white foam (397 mg, 79%). Rf = 0.27 (PE:EtOAc = 2:1); [alpha]D20 = -31.8 (c = 0.4, CH2Cl2); 1H NMR (400 MHz, CDCl3), delta (ppm): 7.94 (m, 2H, 2 HAr), 7.46 (d, J = 7.6 Hz, 1H, HAr), 7.40 (t, J = 8.0 Hz, 1H, HAr), 5.36 (d, J = 2.9 Hz, 1H, H4), 5.26 (dd, J = 10.4, 8.0 Hz, 1H, H2), 4.97 (dd, J = 10.5, 3.4 Hz, 1H, H3), 4.91 (d, J = 12.6 Hz, 1H, OCH2a), 4.65 (d, J = 12.6 Hz, 1H, OCH2b), 4.51 (d, J = 8.0 Hz, 1H, H1), 4.21-4.06 (m, 2H, H6), 3.91-3.85 (m, 4H, OMe, H5), 2.13 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 1.95 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3), delta (ppm): 170.5 (C=O), 170.3 (C=O), 170.2 (C=O), 169.6 (C=O), 166.8 (COOMe), 137.3 (CAr), 132.2 (CAr-H), 130.4 (CAr), 129.2 (CAr-H), 128.70 (CAr-H), 128.65 (CAr-H), 100.0 (C1), 70.9 (C3), 70.8 (C5), 70.1 (OCH2), 68.8 (C2), 67.1 (C4), 61.3 (C6), 52.2 (OMe), 20.7 (3 × COCH3), 20.6 (COCH3); HRMS m/z: calcd. for C23H28NaO12, [M+Na]+ 519.1473, found 519.1466. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44%; 37% | With boron trifluoride diethyl etherate; In dichloromethane; at -20℃; for 2h;Inert atmosphere; | Entry 26 Boron trifluoride etherate (7 muL, 0.056 mmol, 0.2 eq.) was added dropwise at -20C under argon to a stirred solution of 2,3,4,6-tetra-O-acetyl-alpha-d-galactopyranosyl trichloroacetimidate (1c) (209 mg, 0.424 mmol, 1.5 eq.) and <strong>[67853-03-6]methyl 3-hydroxymethylbenzoate</strong> (2d) (47 mg, 0.283 mmol, 1 eq.) in freshly distilled CH2Cl2 (3 mL). After 2 hours, Et3N (0.2 mL) was injected into the reaction mixture. Then, the solvent was evaporated, the residue was purified by silica gel column chromatography (PE:EtOAc, 5:1 to 3:1) to afford (1-methoxycarbonylphen-3-yl)methyl 2,3,4,6-tetra-O-acetyl-beta-d-galactoside (3e) as a white foam (62 mg, 44%) and acetylated acceptor (22 mg, 37%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.46 g | With boron trifluoride diethyl etherate; In dichloromethane; at -40℃; for 25h; | 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl2,2,2-trichloroacetimidate (Tokyo Chemical Industry Co., LTD., Japan; T2295,0.32 g, 0.61 mmol) was dissolved in 15 mL dry CH2Cl2 andadded to <strong>[126070-20-0]4-((tert-butyldimethylsilyloxy)methyl)phenol</strong>(0.22 g, 0.91 mmol, see references 5-7) in 5 mL of CH2Cl2at -40C and then added boron trifluoride - ethyl ether complex (10 µL, 0.061 mmol). Afterstirring at -40C for 25 h, themixture was poured into ethyl acetate. The organic layer was washed withsaturated NaHCO3 (aq) and saturated NaCl (aq), and then dried overNa2SO4. The residue obtained was purified by columnchromatography on silica gel (2: 1, hexane: ethyl acetate) to afford 0.46 g ofcompound 7. Obtained compound 7 was dissolved in 10 mL methanol andadded to DOWEX50W-X8 H+form (92.5 mg). After stirring for9 h, the mixture was filtered. The residue obtained was purified by columnchromatography on silica gel (1: 2, hexane: ethyl acetate) to afford 0.20 g (71.7%yield) of compound 8. Chauvin, T. et al.have been reported synthesis and instrumental analysis of compound 8 in Angew. Chem. Int. Ed. 2008,47, 4370-4372. NMR and ESI-MS data of compound 8 are consistent with the reported data. |