N-Deformyl-N-benzyloxycarbonyl Orlistat

Base Information

• Chemical Name: N-Deformyl-N-benzyloxycarbonyl Orlistat
• CAS No.: 108051-94-1
• Molecular Formula: C36H59NO6
• Molecular Weight: 601.868
• ChEMBL ID: CHEMBL453289
• DSSTox Substance ID: DTXSID30564645
• Nikkaji Number: J1.175.895I
• Wikidata: Q82449420
• Mol file: 108051-94-1.mol

Synonyms:N-Deformyl-N-benzyloxycarbonyl Orlistat;108051-94-1;CHEMBL453289;[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoate;N-[(PhenylMethoxy)carbonyl]-L-Leucine (1S)-1-[[(2S,3S)-3-Hexyl-4 -oxo-2-oxetanyl]Methyl]dodecyl Ester;SCHEMBL715188;DTXSID30564645;(2S)-1-[(2S,3S)-3-HEXYL-4-OXOOXETAN-2-YL]TRIDECAN-2-YL (2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-4-METHYLPENTANOATE;BDBM50274725;J-002048;(S)-1-((2S,3S)-3-Hexyl-4-oxooxetan-2-yl)tridecan-2-yl ((benzyloxy)carbonyl)-L-leucinate;(2S)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-[(benzyloxy)carbonyl]-L-leucinate;N-[(Phenylmethoxy)carbonyl]-L-leucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester

Chemical Property of N-Deformyl-N-benzyloxycarbonyl Orlistat

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 45-47 °C
• Boiling Point: 685.897oC at 760 mmHg
• PKA: 10.94±0.46(Predicted)
• Flash Point: 368.617oC
• PSA: 94.42000
• Density: 1.018g/cm3
• LogP: 9.26670
• XLogP3: 11.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 26
• Exact Mass: 601.43423860
• Heavy Atom Count: 43
• Complexity: 765

Purity/Quality:

97% ^*data from raw suppliers

N-Deformyl-N-benzyloxycarbonylOrlistat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC(=O)OCC2=CC=CC=C2
• Uses: Orlistat analogue.

Technology Process of N-Deformyl-N-benzyloxycarbonyl Orlistat

There total 67 articles about N-Deformyl-N-benzyloxycarbonyl Orlistat 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: 95.0%

Z-Leu-OH (2018-66-8) + (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one (104871-99-0,104872-00-6,104872-03-9,104872-05-1,104872-06-2,104872-07-3,104872-19-7,68711-40-0) → N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (108051-94-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1039/a904533c

Reference yield: 77.0%

carbon monoxide (201230-82-2) + (S)-1-((2S,3R)-3-hexyloxiran-2-yl)tridecan-2-yl ((benzyloxy)carbonyl)-L-leucinate (1620408-84-5) → N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (108051-94-1)

Guidance literature:

With dicobalt octacarbonyl; chlorochromium(III) meso-tetrakis(4-chlorophenyl)porphyrinate; In tetrahydrofuran; at 60 ℃; for 16h; under 46544.6 Torr;

DOI:10.1021/acsinfecdis.1c00283

Reference yield:

acrylic acid 1-undecyl-but-3-enyl ester → N-[(phenylmethoxy)carbonyl]-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (108051-94-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 93 percent / Ti(O-i-Pr)4 / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 40 °C

2.1: NaOH; H₂O₂ / H₂O / 23 °C

3.1: 83 percent / NaBH₄; PhSeSePh; AcOH / propan-2-ol / 0 °C

4.1: 98 percent / (i-Pr)2NEt / dimethylformamide / 12 h / 23 °C

5.1: 75 percent / NEt₃ / 12 h / 23 °C

6.1: PPTS / 8 h

7.1: Bu₄NF; AcOH / tetrahydrofuran / 5 h / 23 °C

8.1: LDA; HMPA / tetrahydrofuran / 2 h / -78 - -50 °C

8.2: tetrahydrofuran / 6 h / -78 - 0 °C

9.1: LiOH; H₂O / 12 h / 25 °C

10.1: PhSO₂Cl; pyridine / 8 h / 0 °C

11.1: 90 percent / PPTS / ethanol / 3 h / Heating

12.1: 95 percent / DCC; DMAP

With pyridine; titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; diphenyl diselenide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 1.1: Cyclization / 2.1: Epoxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Esterification / 6.1: Etherification / 7.1: desilylation / 8.1: Metallation / 8.2: Alkylation / 9.1: Hydrolysis / 10.1: Cyclization / 11.1: acidolysis / 12.1: Esterification;

DOI:10.1039/a904533c

upstream raw materials:

Z-Leu-OH

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

Dodecanal

(2E,4E)-hexadecadienoic acid

Downstream raw materials:

Orlistat