(4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide

Base Information

• Chemical Name: (4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide
• CAS No.: 866030-36-6
• Molecular Formula: C26H44N2O7
• Molecular Weight: 496.645
• DSSTox Substance ID: DTXSID50704869
• Nikkaji Number: J2.214.494D
• Mol file: 866030-36-6.mol

Synonyms:866030-36-6;(4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide;tert-butyl N-[(2S,4S)-4-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-1-[methoxy(methyl)amino]-5-methyl-1-oxohexan-2-yl]carbamate;DTXSID50704869;AKOS025402373;AC-8493;(2S,4S)-N-Methoxy-N,5-dimethyl-2-(tert-butoxycarbonylamino)-4-[3-(3-methoxypropoxy)-4-methoxybenzyl]hexanamide

Chemical Property of (4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide

Chemical Property:

• Refractive Index: 1.495
• PSA: 104.35000
• Density: 1.068 g/cm³
• LogP: 4.71050
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 16
• Exact Mass: 496.31485175
• Heavy Atom Count: 35
• Complexity: 623

Purity/Quality:

98%Min ^*data from raw suppliers

[(1S,3S)-3-[[4-METHOXY-3-(3-METHOXYPROPOXY)PHENYL]METHYL]-1-[(METHOXYMETHYLAMINO)CARBONYL]-4-METHYLPENTYL]CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CC(C(=O)N(C)OC)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)C[C@@H](C(=O)N(C)OC)NC(=O)OC(C)(C)C

Technology Process of (4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide

There total 11 articles about (4S)-N~2~-(tert-Butoxycarbonyl)-N-methoxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-N,5-dimethyl-L-norleucinamide 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:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → [(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester (866030-36-6)

Guidance literature:

Multi-step reaction with 11 steps

1: NaBH₄ / ethanol

2: PBr₃ / CH₂Cl₂

3: 76 percent / LiHMDS / tetrahydrofuran

4: 81 percent / LiOH; H₂O₂

5: 95 percent / LAH / tetrahydrofuran

6: 97 percent / PPh₃; NBS / CH₂Cl₂

7: 68 percent / n-BuLi

8: HCl / acetonitrile

9: Et₃N

10: LiOH / methanol; H₂O

11: EDCI; HOBt

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; phosphorus tribromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid (172900-71-9) → [(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester (866030-36-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / LAH / tetrahydrofuran

2: 97 percent / PPh₃; NBS / CH₂Cl₂

3: 68 percent / n-BuLi

4: HCl / acetonitrile

5: Et₃N

6: LiOH / methanol; H₂O

7: EDCI; HOBt

With hydrogenchloride; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

Reference yield:

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine (866030-33-3) → [(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester (866030-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / acetonitrile

2: Et₃N

3: LiOH / methanol; H₂O

4: EDCI; HOBt

With hydrogenchloride; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; water; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine

isovanillin

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

Downstream raw materials:

Benzyl-[(1S,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester

Benzyl-{(1S,3S)-1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

((1S,2R,4S)-2-Hydroxy-4-hydroxymethyl-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

Benzyl-((1S,2R,4S)-4-benzyloxymethyl-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester