1'N-Benzyl Biotin

Base Information

• Chemical Name: 1'N-Benzyl Biotin
• CAS No.: 76335-62-1
• Molecular Formula: C17H22N2O3S
• Molecular Weight: 334.439
• DSSTox Substance ID: DTXSID60438027
• Wikidata: Q82253635
• Mol file: 76335-62-1.mol

Synonyms:1'N-Benzyl Biotin;76335-62-1;5-[(3aR,6S,6aS)-3-benzyl-2-oxo-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentanoic acid;(3aS,4S,6aR)-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno[3,4-d]imidazole-4-pentanoic Acid;N-Benzyl-d-biotin;1/'N-Benzyl Biotin;DTXSID60438027;1 inverted exclamation mark N-Benzyl Biotin

Chemical Property of 1'N-Benzyl Biotin

Chemical Property:

• PSA: 98.43000
• LogP: 2.28730
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 334.13511374
• Heavy Atom Count: 23
• Complexity: 440

Purity/Quality:

NLT 98% ^*data from raw suppliers

1’N-BenzylBiotin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2CC3=CC=CC=C3
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)O)NC(=O)N2CC3=CC=CC=C3
• Uses: As a biotin derivative, 1'N-Benzyl Biotin can be used in the novel enantioselective syntheses of (+)-Biotin.

Technology Process of 1'N-Benzyl Biotin

There total 27 articles about 1'N-Benzyl Biotin 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:

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester (151526-81-7) → 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid (76335-62-1)

Guidance literature:

With sodium hydroxide; water; In methanol; at 40 ℃; for 3h;

DOI:10.1021/jo025794+

Reference yield:

benzaldehyde (100-52-7) → 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid (76335-62-1)

Guidance literature:

Multi-step reaction with 5 steps

1: citric acid; NaHCO₃; NaBH₃CN / H₂O; tetrahydrofuran / 2.5 h / 5 °C / pH 4

2: 1.4 g / HCl / H₂O; tetrahydrofuran / 21 h / 25 °C

3: 77 percent / NaHCO₃; triethyl phosphite; Pd(OAc)2 / tetrabutylammonium chloride / dimethylformamide; H₂O / 2 h / 100 °C

4: 100 percent / hydrogen / 10percent Pd(OH)2 on carbon / ethyl acetate / 2 h / 25 °C / 4 Torr

5: water; NaOH / methanol / 3 h / 40 °C

With hydrogenchloride; palladium diacetate; sodium hydroxide; water; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; citric acid; triethyl phosphite; tetrabutyl-ammonium chloride; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo025794+

Reference yield:

<3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester (151526-80-6) → 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid (76335-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / hydrogen / 10percent Pd(OH)2 on carbon / ethyl acetate / 2 h / 25 °C / 4 Torr

2: water; NaOH / methanol / 3 h / 40 °C

With sodium hydroxide; water; hydrogen; 10percent Pd(OH)2 on carbon; In methanol; ethyl acetate;

DOI:10.1021/jo025794+

upstream raw materials:

-(3,6,7,8,9,10-Hexahydro-10-oxo-2H-thiecin-3-yl)-(phenylmethyl)carbamoyl azide

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

benzaldehyde

<3aS-(3aα,4Z,6aα)>-5-imidazol-4-ylidene>pentanoic acid methyl ester

Downstream raw materials:

biotin

vitamin H

(+/-)-5-[1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid methyl ester

Refernces

• 1、 Deroose, Frederik D.,De Clercq, Pierre J.. "Novel Enantioselective Syntheses of (+)-Biotin". . p. 321 - 330. Retrieved 2007/10/02.