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1279691-36-9

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Basic Information
CAS No.: 1279691-36-9
Name: (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol
Article Data: 13
Molecular Structure:
Molecular Structure of 1279691-36-9 ((2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol)
Formula: C24H29ClO8
Molecular Weight: 480.942
Synonyms: (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol;Methyl 1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]Methyl]phenyl]-alpha-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol;Empagliflozin Intermediate3;Empagliflozin Intermediates;(3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
EINECS: 1592732-453-0
Density: 1.43±0.1 g/cm3(Predicted)
Boiling Point: 663.4±55.0 °C(Predicted)
PSA: 117.84000
LogP: 1.37150
Related products
Synthetic route
67-56-1

methanol

1279691-35-8

(2S,3R,4S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 30℃; for 1h;90.5%
With hydrogenchloride In water at 20℃; pH=0; Product distribution / selectivity;
With trifluoroacetic acid at 20℃; for 5h; Reagent/catalyst; Large scale;10 kg
67-56-1

methanol

915095-89-5

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Large scale;		87%
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Inert atmosphere; Large scale;
Stage #2: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Inert atmosphere; Large scale;		84%
...Expand
915095-89-5

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 1h; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -78℃; for 3h; Large scale;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at 0 - 40℃; for 10h; Large scale;		84%
915095-94-2

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

C18H42O6Si4

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;77.6%
75-75-2

methanesulfonic acid

C35H58ClO8Si4(1-)*Li(1+)

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
In methanol at 20℃; for 10h;76.3%
915095-87-3

(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
2: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
3: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
4: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
915095-94-2

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
2: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
3: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
Multi-step reaction with 2 steps
1: lithium chloride; isopropylmagnesium chloride / tetrahydrofuran / -30 - -20 °C / Inert atmosphere; Large scale
2: hydrogenchloride / methanol; water / 4 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: TurboGrignard / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere
1.2: 0.5 h / Inert atmosphere
2.1: hydrogenchloride / water / 1 h / 20 - 30 °C
View Scheme

C35H59ClO8Si4

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
2: hydrogenchloride / isopropyl alcohol; methanol
View Scheme

C24H29ClO8

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With hydrogenchloride In methanol; isopropyl alcohol204 g
19094-56-5

2-chloro-5-iodobenzoic acid

1279691-36-9

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 2 h / 15 - 25 °C
2: aluminum (III) chloride / 1 h / 0 - 25 °C
3: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C
4: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C
5: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C
6: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2
7: hydrogenchloride / isopropyl alcohol; methanol
View Scheme
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