ChemicalBook CAS DataBase List Dapagliflozin Tetraacetate

Dapagliflozin Tetraacetate synthesis

8synthesis methods

Product Name:Dapagliflozin Tetraacetate
CAS Number:461432-25-7
Molecular formula:C29H33ClO10
Molecular Weight:577.02

1103738-29-9 Synthesis

1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene

1103738-29-9
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$8.00/250mg

2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL BROMIDE

6919-96-6
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461432-25-7
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$65.00/100mg

Yield:461432-25-7 281.2 g

Reaction Conditions:

Stage #1: 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzenewith iodine;magnesium in tetrahydrofuran at 35; for 5 h;Inert atmosphere;
Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromidewith gallium(III) oxide in toluene at -20 - 5; for 2 h;Inert atmosphere;Reagent/catalyst;

Steps:

1-4 Example 2

Weigh 26.7g (1.33mol) of activated magnesium, add two more iodine particles, and heat to 35 under the protection of nitrogen,Then add 500mL of anhydrous THF to it without magnesium, and then add 200mL of 10% iodobenzene in THF solution (total 2000mL: 20g iodobenzene 0.53mol) + 2000mLTHF). The remaining iodobenzene solution was added dropwise, reacted for 5h, and filtered to obtain the Grignard reagent THF solution of iodobenzene.Weigh 217.83g 2,3,4,6-tetraacetylbromoglucose (0.53mol) dissolved in 5000mL toluene, then add 5.76g gadolinium oxide (3mol%),Under nitrogen protection, the temperature was reduced to -20 ° C, and the prepared iodobenzene Grignard was added dropwiseControl the temperature at -20 -15 . After the dropwise addition, increase the temperature to 5 for 2h, concentrate to an oil in vacuo, then add 2000mL of toluene to dissolve it, then extract twice with saturated aqueous sodium chloride solution, and dry the organic phase , Concentrate in vacuo to an oil, then add 1000mL 3: 1 n-hexane / ethyl acetate solution, heat to dissolve, cool, precipitate solid, filter and dry to obtain 281.2g of solid, yield 92.1%.

References:

CN111057032,2020,A Location in patent:Paragraph 0034; 0035; 0037; 0040; 0041; 0043; 0045; 0046

461432-26-8 Synthesis