76335-62-1

Basic information

• Product Name: 1'N-Benzyl Biotin
• Synonyms: 1'N-Benzyl Biotin;(3aS,4S,6aR)-;1a€N-Benzyl Biotin
• CAS NO: 76335-62-1
• Molecular Formula: C₁₇H₂₂N₂O₃S
• Molecular Weight: 334.43
• Product Categories: Aromatics;Biotin Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 76335-62-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: 1'N-Benzyl Biotin(CAS DataBase Reference)
• NIST Chemistry Reference: 1'N-Benzyl Biotin(76335-62-1)
• EPA Substance Registry System: 1'N-Benzyl Biotin(76335-62-1)

Safety Data

• Hazardous Substances Data: 76335-62-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1'N-Benzyl Biotin is used as a key intermediate in the novel enantioselective syntheses of (+)-Biotin for the pharmaceutical industry. The enantioselective synthesis allows for the production of optically pure (+)-Biotin, which is essential for its biological activity and therapeutic applications.
As a biotin derivative, 1'N-Benzyl Biotin can also be utilized in the development of new drugs and therapies that target biotin-dependent enzymes and pathways, potentially leading to innovative treatments for various diseases and conditions.
In addition to its applications in the pharmaceutical industry, 1'N-Benzyl Biotin may also find use in other industries, such as cosmetics, agriculture, and research, where biotin and its derivatives are known to have beneficial effects. However, the specific applications and reasons for using 1'N-Benzyl Biotin in these industries are not provided in the given materials.

Upstream product

• 100-52-7 benzaldehyde 
• 151526-81-7 <3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester 
• 157020-40-1 -(3,6,7,8,9,10-Hexahydro-10-oxo-2H-thiecin-3-yl)-(phenylmethyl)carbamoyl azide 
• 31860-26-1 5-(1,3-dibenzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid 
• 157020-38-7 (Z)-(R)-9-Amino-3,4,5,6,9,10-hexahydro-thiecin-2-one 
• 161458-85-1 (Z)-(R)-9-{[1-Phenyl-meth-(E)-ylidene]-amino}-3,4,5,6,9,10-hexahydro-thiecin-2-one 
• 157020-36-5 cis-8(R)-<(tert-Butoxycarbonyl)amino>-9-mercaptonon-6-enoic acid 
• 157020-35-4 cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 157020-37-6 1,1-Dimethylethyl -(3,6,7,8,9,10-hexahydro-10-oxo-2H-thiecin-3-yl)carbamate 
• 157020-39-8 (Z)-(R)-9-Benzylamino-3,4,5,6,9,10-hexahydro-thiecin-2-one 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 4224-70-8 6-bromohexanoic acid 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 

Downstream Products

• 58-85-5 biotin 
• 58-85-5 vitamin H 
• 77566-74-6 (+/-)-5-[1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid methyl ester 

Relevant articles and documents

A novel synthesis of (+)-biotin from L-cysteine

(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.

Novel Enantioselective Syntheses of (+)-Biotin

Two conceptually attractive enantioselective syntheses of (+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide.The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of (+)-biotin 16a and 17a.The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b.Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

A novel enantioselective synthesis of (+)-biotin

A conceptually attractive enantioselective 12-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cycloaddition sequence involving as key-steps (i) the macrothiolactonisation of acid 3 to Z-olefin (4), (ii) the thermolysis of the ene carbamoyl azide 5 in water with direct formation of a mixture of the benzylated derivative of (+)-biotin 6a and 6b.