(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol supplier

Name
(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol
EINECS
CAS No. 156732-15-9
Article Data16
CAS DataBase
Density 1.125 g/cm³
Solubility
Melting Point
Formula C₃₂H₃₆N₂O
Boiling Point 642.878 °C at 760 mmHg
Molecular Weight 464.651
Flash Point 342.601 °C
Transport Information
Appearance Colourless thick oil
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzenebutanol,g-amino-a-[1-[bis(phenylmethyl)amino]-2-phenylethyl]-,[aS-[aR*(R*),gR*]]-;(2S,3S,5S)-5-Amino-2-(dibenzylamino)-3-hydroxy-1,6-diphenylhexane;
PSA 49.49000
LogP 6.32140

Synthetic route

: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid at 6℃; for 1.5h; Stage #2: With sodium tetrahydroborate; trifluoroacetic acid at 6℃; for 1.5h;	93%
Stage #1: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid In tetrahydrofuran; isopropyl alcohol at 0 - 10℃; Stage #2: With trifluoroacetic acid In tetrahydrofuran; isopropyl alcohol at 0 - 15℃; for 4.75h;	55%
Stage #1: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid In 1,2-dimethoxyethane; isopropyl alcohol at -5℃; for 12h; Stage #2: With triethanolamine In 1,2-dimethoxyethane; isopropyl alcohol at -5℃; for 0.5h; Stage #3: In 1,2-dimethoxyethane; N,N-dimethyl acetamide; isopropyl alcohol at 0℃; for 2h;	40%

: (S,E)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: (S,E)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one With sodium tetrahydroborate; methanesulfonic acid In diethylene glycol dimethyl ether; isopropyl alcohol at 0 - 5℃; for 12h; Stage #2: With triethanolamine In diethylene glycol dimethyl ether; isopropyl alcohol at 0 - 5℃; for 0.5h; Stage #3: With sodium tetrahydroborate In diethylene glycol dimethyl ether; N,N-dimethyl acetamide; isopropyl alcohol at 15℃; for 3h;	65%

Yield

Stage #1: (S,E)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one With sodium tetrahydroborate; methanesulfonic acid In diethylene glycol dimethyl ether; isopropyl alcohol at 0 - 5℃; for 12h;
Stage #2: With triethanolamine In diethylene glycol dimethyl ether; isopropyl alcohol at 0 - 5℃; for 0.5h;
Stage #3: With sodium tetrahydroborate In diethylene glycol dimethyl ether; N,N-dimethyl acetamide; isopropyl alcohol at 15℃; for 3h;

65%

: 7440-06-4
platinum

: 2-Amino-5-S-N,N-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
With methanesulfonic acid; hydrogen In ethanol
With methanesulfonic acid; hydrogen In ethanol

: 2-amino-5S-dibenzylamino-4-oxo-1,6-diphenylhexane

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: 2-amino-5S-dibenzylamino-4-oxo-1,6-diphenylhexane With sodium tetrahydroborate; methanesulfonic acid In 1,2-dimethoxyethane; isopropyl alcohol at 15 - 25℃; for 1h; Stage #2: With triethanolamine In ISOPROPYLAMIDE; water at 10 - 30℃; for 0.5h;
Stage #1: 2-amino-5S-dibenzylamino-4-oxo-1,6-diphenylhexane With sodium tetrahydroborate; methanesulfonic acid In 1,2-dimethoxyethane; isopropyl alcohol at 20℃; for 6h; Stage #2: With triethanolamine In ISOPROPYLAMIDE at 15℃; for 1h;

: 220887-32-1
(5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: (5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid In Dimethyl ether; isopropyl alcohol at 0 - 10℃; for 12.5h; Stage #2: With triethanolamine In Dimethyl ether; ISOPROPYLAMIDE; isopropyl alcohol at 0 - 20℃; for 2.91667h; Stage #3: With water In Dimethyl ether; ISOPROPYLAMIDE; isopropyl alcohol at 10 - 20℃;

: 2-Amino-5-S-N,N-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
With sodium borohydrid; methanesulfonic acid In 1,2-dimethoxyethane; tert-butyl methyl ether; ISOPROPYLAMIDE; isopropyl alcohol

: 172526-43-1
(5S,1'S)-3-phenylmethyl-5-(1'-N,N-dibenzylamino-2'-phenylethyl)-2-isoxazoline

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
With sodium hydroxide In di-isopropyl ether; water
Pt-on-carbon In ethanol; ammonia

: (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane L-pyroglutamic acid

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 25 - 30℃; for 0.25h;

: 156732-14-8
(2S,5S)-5-amino-2-dibenzylamino-3-oxo-1,6-diphenylhexane

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: (2S,5S)-5-amino-2-dibenzylamino-3-oxo-1,6-diphenylhexane With sodium tetrahydroborate; trifluoroacetic acid In 1,2-dimethoxyethane at -10 - 20℃; for 0.5h; Stage #2: With sodium hydroxide In 1,2-dimethoxyethane; water at 5 - 10℃;

: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene

A: (2S,3R,5R)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

B: (2S,3S,5S)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

C: (2S,3S,5R)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

D: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Stage #1: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid; isopropyl alcohol In 1,2-dimethoxyethane at 0 - 10℃; for 12h; Stage #2: With triethanolamine In 1,2-dimethoxyethane at 5℃; for 0.5h; Stage #3: With sodium tetrahydroborate In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 10 - 20℃; for 2h; Reagent/catalyst; Solvent; diastereoselective reaction;	A n/a B n/a C n/a D n/a

Yield

Stage #1: (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene With sodium tetrahydroborate; methanesulfonic acid; isopropyl alcohol In 1,2-dimethoxyethane at 0 - 10℃; for 12h;
Stage #2: With triethanolamine In 1,2-dimethoxyethane at 5℃; for 0.5h;
Stage #3: With sodium tetrahydroborate In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 10 - 20℃; for 2h; Reagent/catalyst; Solvent; diastereoselective reaction;

A n/a
B n/a
C n/a
D n/a

...Expand

: 63-91-2
L-phenylalanine

A: (2S,3R,5R)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

B: (2S,3S,5S)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

C: (2S,3S,5R)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane

D: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; potassium hydroxide / water / 5 h / Reflux 2.1: sodium amide / acetonitrile; tert-butyl methyl ether / 2 h / 0 - 5 °C / Large scale 2.2: 2 h / 25 °C / Large scale 3.1: sodium tetrahydroborate; methanesulfonic acid; isopropyl alcohol / 1,2-dimethoxyethane / 12 h / 0 - 10 °C 3.2: 0.5 h / 5 °C 3.3: 2 h / 10 - 20 °C View Scheme

...Expand

: 111138-83-1
N,N-dibenzyl-L-phenylalanine benzyl ester

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium amide / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere 1.2: 3 h / -45 °C / Inert atmosphere 2.1: tetrahydrofuran / 0 - 20 °C 3.1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; isopropyl alcohol / 0 - 10 °C 3.2: 4.75 h / 0 - 15 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium amide 2.1: 10 h / 5 °C 3.1: sodium tetrahydroborate; methanesulfonic acid / 1.5 h / 6 °C 3.2: 1.5 h / 6 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium amide / tert-butyl methyl ether / 2 h / -5 - 0 °C 1.2: 2 h / 20 °C 1.3: 0 °C 2.1: sodium tetrahydroborate; methanesulfonic acid / diethylene glycol dimethyl ether; isopropyl alcohol / 12 h / 0 - 5 °C 2.2: 0.5 h / 0 - 5 °C 2.3: 3 h / 15 °C View Scheme

: 6921-34-2
benzylmagnesium chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 - 20 °C 2.1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; isopropyl alcohol / 0 - 10 °C 2.2: 4.75 h / 0 - 15 °C View Scheme
Multi-step reaction with 2 steps 1.1: 10 h / 5 °C 2.1: sodium tetrahydroborate; methanesulfonic acid / 1.5 h / 6 °C 2.2: 1.5 h / 6 °C View Scheme

: 4S-N,N-dibenzylamino-3-oxo-5-phenylvaleronitrile

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 10 h / 5 °C 2.1: sodium tetrahydroborate; methanesulfonic acid / 1.5 h / 6 °C 2.2: 1.5 h / 6 °C View Scheme

: 253265-97-3
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 24h;	100%

: 24601-74-9
(S)-4-isopropyloxazolidine-2,5-dione

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: (S)-2-amino-N-[(2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methylbutanamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -15℃; for 4h; Inert atmosphere;	97%

: 6949-76-4
1-((methoxycarbonyl)amino)cyclopentane-1-carboxylic acid

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: methyl (1-(((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)carbamoyl)cyclopentyl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	95%

: 13335-71-2
2-(2,6-dimethylphenoxy)acetic acid

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 898254-22-3
N-((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;	90%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	86%

: 1239660-25-3
(S)-2-cyclopentyl-2-((methoxycarbonyl)amino)acetic acid

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: methyl ((S)-1-cyclopentyl-2-(((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)amino)-2-oxoethyl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	90%

: 24424-99-5
di-tert-butyl dicarbonate

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 162849-93-6
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

Conditions

Conditions	Yield
With potassium carbonate at 16℃; for 11h;	88%

: 162537-11-3
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: methyl ((S)-1-(((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	87%
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h; Further stages.;

Yield

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 4h;

87%

Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h; Further stages.;

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 74-88-4
methyl iodide

: C33H38N2O

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 5h;	17%

: 1066876-06-9
2-oxo-3-phenyl-oxazolidine-5-carbonyl chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C42H43N3O4

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 8h;

: 1066875-99-7
2-oxo-3-phenyl-oxazolidine-5-carbonyl chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C42H43N3O4

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 8h;

: 1066876-02-5
2-oxo-3-(3-trifluoromethyl-phenyl)-oxazolidine-5-carbonyl chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C43H42F3N3O4

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 8h;

: 96-81-1
N-acetyl-L-valine

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C39H47N3O3

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water at 0 - 4℃; for 24h;

: 192800-77-4
2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 192726-04-8
(2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane

Conditions

Conditions	Yield
With 1H-imidazole In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃;
With 1H-imidazole In DMF (N,N-dimethyl-formamide); ethyl acetate at 2℃;
With 1H-imidazole In ethyl acetate at 1℃; for 1.5h;

: 20143-48-0
2,6-dimethylphenoxyacetyl chloride

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 898254-22-3
N-((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 1h;

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 192726-05-9
(2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide; ethyl acetate / 0 - 20 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C 1.2: 4 h / 70 - 75 °C 2.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C25H35N3O3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 854754-08-8
methyl (1S)-1-({[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: EDCl; HOBt / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 1.2: DIPEA / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C 2.1: HCO2NH4 / Pd/C / methanol / 50 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2: ammonium formate; palladium 10% on activated carbon / methanol / 15 h / 50 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C35H42N4O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C35H42N4O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C35H40F2N4O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C36H41F3N4O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C37H44N4O7

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: EDCl; HOBt / H2O; CH2Cl2 / 24 h / 0 - 4 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C37H45N5O6

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: imidazole / dimethylformamide; ethyl acetate / 0 - 20 °C 2: HCO2NH4 / Pd/C / methanol / 50 °C 3: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: C36H44N4O7

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: EDCl; HOBt / dimethylformamide; CH2Cl2 / 0.25 h / 0 °C 1.2: DIPEA / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C 2.1: HCO2NH4 / Pd/C / methanol / 50 °C 3.1: Et3N / tetrahydrofuran / 8 h / 0 - 20 °C View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 144163-85-9
(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(OH)2; HCO2NH4 View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / 20 °C 2: palladium on activated charcoal; ammonium formate; water / ethanol / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1 h / 20 °C 2: palladium 10% on activated carbon; ammonium formate / ethanol; water / 3 h / Reflux View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-49-8
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Pd(OH)2; HCO2NH4 2: EDC 3: trifluoroacetic acid View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 1 h / 20 °C 2: palladium on activated charcoal; ammonium formate; water / ethanol / 3 h / Reflux 3: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 10 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

: 156732-15-9
(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

: 192725-45-4
(2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Pd(OH)2; HCO2NH4 2: EDC View Scheme
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h / 20 °C 2: palladium on activated charcoal; ammonium formate; water / ethanol / 3 h / Reflux 3: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 10 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h / 20 °C 2: palladium 10% on activated carbon; ammonium formate / ethanol; water / 3 h / Reflux 3: 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C View Scheme

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Chemical Properties

Molecule structure of (2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol (CAS NO.156732-15-9):

Molecular Weight: 464.64 g/mol
Molecular Formula: C₃₂H₃₆N₂O
Density: 1.125 g/cm³
Boiling Point: 642.878 °C at 760 mmHg
Flash Point: 342.601 °C
Index of Refraction: 1.624
Molar Refractivity: 145.729 cm³
Molar Volume: 412.963 cm³
Polarizability: 57.772×10^-24 cm³
Surface Tension: 50.823 dyne/cm
Enthalpy of Vaporization: 99.705 kJ/mol
InChI: InChI=1/C32H36N2O/c33-30(21-26-13-5-1-6-14-26)23-32(35)31(22-27-15-7-2-8-16-27)34(24-28-17-9-3-10-18-28)25-29-19-11-4-12-20-29/h1-20,30-32,35H,21-25,33H2/t30-,31-,32-/m0/s1
InChIKey: SRVJQTROLWUZRB-CPCREDONBR
Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Uses

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol (CAS NO.156732-15-9) is used as an intermediate in the synthesis of Ritonavir.

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Specification

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol (CAS NO.156732-15-9) is also named as (2S,3S,5S)-5-amino-2-(dibenzylamino)-3-hydroxy-1,6-diphenylhexane ; Benzenebutanol,g-amino-a-[1-[bis(phenylmethyl)amino]-2-phenylethyl]-,[aS-[aR*(R*),gR*]]- .

Product Name

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol

Synthetic route

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Chemical Properties

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Uses

(2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol Specification

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