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Basic Information
CAS No.: 156732-15-9
Name: (2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol
Molecular Structure:
Molecular Structure of 156732-15-9 ((2S,3S,5S)-5-Amino-2-(benzylamino)-1,6-diphenylhexan-3-ol)
Formula: C32H36N2O
Molecular Weight: 464.651
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;
Density: 1.125 g/cm3
Boiling Point: 642.878 °C at 760 mmHg
Flash Point: 342.601 °C
Appearance: Colourless thick oil
PSA: 49.49000
LogP: 6.32140
Related products
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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Chemistry

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

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.

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*]]- .