(3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid

Base Information

• Chemical Name: (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid
• CAS No.: 785790-37-6
• Molecular Formula: C₁₅H₂₄N₂O₃
• Molecular Weight: 280.367
• Mol file: 785790-37-6.mol

Synonyms:(3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid

Chemical Property of (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid

There total 8 articles about (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-N-allyl (1-phenylethyl)amine (126275-19-2) → (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid (785790-37-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-Bu₃P; HBF₄ / Pd₂(dba)3 / CHCl₃; diethyl ether / 5 h / 80 °C

1.2: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.3: 31.1 g / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 97 percent / RhCl(PPh₃)3 / acetonitrile; H₂O / 2 h / Heating

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

4.1: I₂ / CH₂Cl₂ / 4 h / 0 °C

5.1: aq. NaN₃ / dimethylformamide / 5 h / 110 °C

5.2: 1.24 g / H₂ / Pd/C / methanol / 28 h / 760 Torr

6.1: 99 percent / aq. LiOH / tetrahydrofuran / 3 h / 20 °C

7.1: aq. KOH / ethanol / 72 h / 80 °C

With dmap; potassium hydroxide; lithium hydroxide; tetrafluoroboric acid; sodium azide; tributylphosphine; iodine; triethylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; RhCl(PPh₃)3; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b404962d

Reference yield:

(3R,5E,αR)-methyl 3-(N-allyl-N-α-methylbenzylamino)hept-5-enoate (624738-97-2) → (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid (785790-37-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / RhCl(PPh₃)3 / acetonitrile; H₂O / 2 h / Heating

2.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

3.1: I₂ / CH₂Cl₂ / 4 h / 0 °C

4.1: aq. NaN₃ / dimethylformamide / 5 h / 110 °C

4.2: 1.24 g / H₂ / Pd/C / methanol / 28 h / 760 Torr

5.1: 99 percent / aq. LiOH / tetrahydrofuran / 3 h / 20 °C

6.1: aq. KOH / ethanol / 72 h / 80 °C

With dmap; potassium hydroxide; lithium hydroxide; sodium azide; iodine; triethylamine; RhCl(PPh₃)3; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b404962d

Reference yield:

(4R,6R,1'R,αR)-3-(N-α-methylbenzyl)-4-(carboxymethyl)-6-(1'-aminoethyl)-1,3-oxazin-2-one (785790-21-8) → (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid (785790-37-6)

Guidance literature:

With potassium hydroxide; In ethanol; at 80 ℃; for 72h;

DOI:10.1039/b404962d

upstream raw materials:

(4R,6R,1'R,αR)-3-(N-α-methylbenzyl)-4-(carboxymethyl)-6-(1'-aminoethyl)-1,3-oxazin-2-one

(3R,5E,αR)-methyl 3-(N-methoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate

(3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate

(R)-N-allyl (1-phenylethyl)amine