[(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester

Base Information

• Chemical Name: [(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester
• CAS No.: 900811-45-2
• Molecular Formula: C₃₀H₄₁NO₇
• Molecular Weight: 527.658
• DSSTox Substance ID: DTXSID90469081
• Wikidata: Q82296657
• Mol file: 900811-45-2.mol

Synonyms:900811-45-2;benzyl N-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-5-oxooxolan-2-yl]pentyl]carbamate;[(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester;BENZYL N-[(1S,3S)-3-{[4-METHOXY-3-(3-METHOXYPROPOXY)PHENYL]METHYL}-4-METHYL-1-[(2S)-5-OXOOXOLAN-2-YL]PENTYL]CARBAMATE;FT-0671255;DTXSID90469081

Chemical Property of [(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester

Chemical Property:

• Boiling Point: 689.9±55.0 °C(Predicted)
• PKA: 11.60±0.46(Predicted)
• Density: 1.132±0.06 g/cm3(Predicted)
• Solubility.: Dichloromethane, Methanol
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 16
• Exact Mass: 527.28830265
• Heavy Atom Count: 38
• Complexity: 696

Purity/Quality:

95% ^*data from raw suppliers

[(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamicAcidBenzylEster ^*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(C2CCC(=O)O2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)C[C@@H]([C@@H]2CCC(=O)O2)NC(=O)OCC3=CC=CC=C3

Technology Process of [(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester

There total 7 articles about [(1S,3S)-3-[[4-Methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamic Acid Benzyl Ester 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:

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid methyl ester (900811-43-0) → phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate (900811-45-2) + phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate

Guidance literature:

With (S)-alpine-hydride; In tetrahydrofuran; at -78 ℃; for 24h;

DOI:10.1021/jo060296c

Reference yield:

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate (900811-40-7) → phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate (900811-45-2)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C

2: 94 percent / EDCI / CH₂Cl₂ / 3.5 h / 0 °C

3: 67 percent / t-BuOH; SmI₂ / tetrahydrofuran / 144 h / -78 °C

4: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C

With sodium hydroxide; samarium diiodide; (S)-alpine-hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo060296c

Reference yield:

(2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoic acid (900811-41-8) → phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate (900811-45-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / EDCI / CH₂Cl₂ / 3.5 h / 0 °C

2: 67 percent / t-BuOH; SmI₂ / tetrahydrofuran / 144 h / -78 °C

3: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C

With samarium diiodide; (S)-alpine-hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo060296c

upstream raw materials:

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid methyl ester

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate

(2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoic acid

pyridin-4-yl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanethioate

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

(5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-aminopentyl]-3-(1-methylethyl)-2(3H)-furanone

(3S,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone

1,1-dimethylethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S,4R)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate

Refernces