Name: (1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol
SKU: 761423-87-4

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Basic Information

Molecular Structure:
CAS No.:	761423-87-4
Name:	(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol
Article Data:	15

Formula:	C21H21FO5S
Molecular Weight:	404.459
Synonyms:	(1S)-1,5-Anhydro-1-C-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-glucitol;Ipragliflozin;ASP-1941/D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, (1S)-;IpragliflozinL-Proline;Ipragliflozin-d3;Ipragliflozin (ASP1941);Ipragliflozin, >=98%
Density:	1.452
Boiling Point:	628.8±55.0 °C(Predicted)
PSA:	118.39000
LogP:	2.14610

Synthetic route

: 1034305-21-9
(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol

A: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

B: (1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

Conditions

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 15℃; for 4h; Temperature; Reagent/catalyst; Concentration; Industrial scale;	A 99.5% B 99%

: 1034305-21-9
(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol With methanol; water; sodium hydroxide at 25 - 49.1℃; Stage #2: With hydrogenchloride In methanol; water at 20.2 - 60℃;	97%
With water; potassium carbonate In toluene at 10℃;	80.1%

: (1S)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-2,3,4,6-tetra-O-pivaloyl-D-glucitol

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
With methanol; sodium methylate at 65℃; for 3h;	95.3%

: 761423-01-2
(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol With boron trichloride In n-heptane; dichloromethane; pentamethylbenzene, at -78℃; for 3h; Inert atmosphere; Stage #2: With methanol In n-heptane; dichloromethane; pentamethylbenzene, at -78℃;	87.8%
With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 4h; Solvent;	75%
Stage #1: (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol With pentamethylbenzene,; boron trichloride In n-heptane; dichloromethane at -78℃; for 4h; Stage #2: With methanol In n-heptane; dichloromethane at -78 - 20℃;	64%
With pentamethylbenzene,; boron trichloride In n-heptane; dichloromethane at -78℃; for 2h;

: C25H29FO5S

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
With triethylsilane; boron trichloride acetic acid In dichloromethane at -20 - 0℃;	71.4%

: C24H27FO5S

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
With triethylsilane; boron trichloride acetic acid In dichloromethane; acetonitrile at -20 - 0℃;	70.2%

: 1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: 1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide at 20℃; for 24h;	49%
Stage #1: 1-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-3,4,6-tri-O-tert-butyldimethylsilyl-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h;	49%
Multi-step reaction with 2 steps 1.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

: 1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: 1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With dihydrogen peroxide; sodium hydroxide at 20℃; for 24h;	45%
Stage #1: 1-(3-(benzo[b]thiophen-2-methyl)-4-fluorophenyl)-3-O-triisopropylsilyl-4,6-O-di-tert-butylsilylene-D-glucal With borane-THF In tetrahydrofuran at 0℃; for 12h; Stage #2: With tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydroxide In water at 20℃; for 24h;	45%

: 1034305-11-7
(1-benzothiophen-2-yl)(5-bromo-2-fluorophenyl)methanol

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 2.2: 2 h / -78 °C 3.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 3.2: -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 2.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 2.2: 2 h / 20 - 90 °C 3.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme

: 1034305-17-3
2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene

: 761423-87-4
(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 1.2: 2 h / -78 °C 2.1: pentamethylbenzene,; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 2.2: -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; dibutyl ether / 3 h / -20 °C 1.2: 1 h / 0 °C 1.3: 3 h / 100 °C 2.1: sodium methylate; methanol / 3 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / dibutyl ether; toluene; n-heptane / 2 h / -40 °C / Inert atmosphere 1.2: 2 h / 20 - 90 °C 2.1: pentamethylbenzene,; boron trichloride / dichloromethane / 4 h / -78 °C View Scheme
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 10 h / 80 °C / Schlenk technique 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine tetrafluoroborate; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C / Sealed tube 3.1: borane-THF / tetrahydrofuran / 12 h / 0 °C 3.2: 24 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

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