tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate

Base Information

• Chemical Name: tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate
• CAS No.: 172900-82-2
• Molecular Formula: C24H41NO6
• Molecular Weight: 439.593
• DSSTox Substance ID: DTXSID40694063
• Mol file: 172900-82-2.mol

Synonyms:172900-82-2;SCHEMBL8904314;DTXSID40694063;FT-0654445;A811468;N-[1-hydroxy-4-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-5-methylhexan-2-yl]carbamic acid tert-butyl ester;tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate;tert-butyl N-[1-(hydroxymethyl)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-pentyl]carbamate

Chemical Property of tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 439.29338803
• Heavy Atom Count: 31
• Complexity: 493

Purity/Quality:

97% ^*data from raw 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(CO)NC(=O)OC(C)(C)C

Technology Process of tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate

There total 20 articles about tert-Butyl (1-hydroxy-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methylhexan-2-yl)carbamate 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: 100.0%

methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate (656241-21-3) → (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol (172900-82-2)

Guidance literature:

methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate; With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 15h;

With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate;

Reference yield: 93.0%

ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate (172900-76-4) → (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol (172900-82-2)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/hlca.200390235

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol (172900-82-2)

Guidance literature:

Multi-step reaction with 10 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: NaBH₄ / ethanol

With hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; phosphorus tribromide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

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

isovanillin

Downstream raw materials:

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

((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

(1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate