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1034305-21-9

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CAS No.: 1034305-21-9
Name: D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-
Article Data: 3
Molecular Structure:
Molecular Structure of 1034305-21-9 (D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-)
Formula: C29H29FO9S
Molecular Weight: 572.608
Synonyms: D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-;(1S)-1,5-Anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-D-glucitol 2,3,4,6-tetraacetate;(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-D-glucitol
Density: 1.35±0.1 g/cm3(Predicted)
Boiling Point: 634.8±55.0 °C(Predicted)
PSA: 142.67000
LogP: 4.42930
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Synthetic route
1034305-27-5

methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside

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

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tert-butyldimethylsilane In toluene; acetonitrile at -9.2 - 1℃;
With triethylsilane; boron trifluoride diethyl etherate In acetonitrile at -5 - 0℃; for 4h; Reagent/catalyst; Temperature;21 g

C21H21FO6S

108-24-7

acetic anhydride

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

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 25℃; for 2h; Temperature; Industrial scale;0.58g
1034305-17-3

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: s-butylmagnesium chloride; n-butyllithium; lithium chloride / tetrahydrofuran; hexane / 3.17 h / -10 °C / Inert atmosphere; Industrial scale
1.2: 3 h / -10 °C / Industrial scale
2.1: pyridine; dmap / dichloromethane / 2 h / 25 °C / Industrial scale
View Scheme
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -60 °C / Inert atmosphere
1.2: 5 h / -60 °C
2.1: sulfuric acid / 20 h / -15 - 10 °C
3.1: dmap; triethylamine / toluene / 5 h / 15 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / -5 - 0 °C
View Scheme
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: s-butylmagnesium chloride; n-butyllithium; lithium chloride / tetrahydrofuran; hexane / 3.17 h / -10 °C / Inert atmosphere; Industrial scale
1.2: 3 h / -10 °C / Industrial scale
2.1: pyridine; dmap / dichloromethane / 2 h / 25 °C / Industrial scale
View Scheme
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1 h / -60 °C / Inert atmosphere
1.2: 5 h / -60 °C
2.1: sulfuric acid / 20 h / -15 - 10 °C
3.1: dmap; triethylamine / toluene / 5 h / 15 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / -5 - 0 °C
View Scheme

C33H53FO6SSi4

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 20 h / -15 - 10 °C
2: dmap; triethylamine / toluene / 5 h / 15 °C
3: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / -5 - 0 °C
View Scheme
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
ConditionsYield
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
ConditionsYield
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%
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