21788-37-4

Basic information

• Product Name: 1H-Thieno[3,4-d]imidazole-4-valeric acid, hexahydro-2-oxo-, stereoisomer (8CI)
• Synonyms: 1H-Thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, [3aR-(3aα,4β,6aα)]-;1H-Thieno[3,4-d]imidazole-4-valeric acid, hexahydro-2-oxo-, stereoisomer (8CI)
• CAS NO: 21788-37-4
• Molecular Formula: C₁₀H₁₆N₂O₃S
• Molecular Weight: 244.31064
• Mol File: 21788-37-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Thieno[3,4-d]imidazole-4-valeric acid, hexahydro-2-oxo-, stereoisomer (8CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Thieno[3,4-d]imidazole-4-valeric acid, hexahydro-2-oxo-, stereoisomer (8CI)(21788-37-4)
• EPA Substance Registry System: 1H-Thieno[3,4-d]imidazole-4-valeric acid, hexahydro-2-oxo-, stereoisomer (8CI)(21788-37-4)

Safety Data

• Hazardous Substances Data: 21788-37-4(Hazardous Substances Data)

Usage

Molecular Class

Thienoimidazole carboxylic acids

Explanation

The compound belongs to a specific class of organic compounds that consist of a thienoimidazole ring and a carboxylic acid group.

Explanation

The compound has a specific three-dimensional arrangement of its atoms, making it a stereoisomer with different spatial orientation.

Explanation

The structure of the compound contains six hydrogen atoms, which are part of its hexahydro configuration.

Explanation

The compound has one oxygen atom in its structure, which is part of the 2-oxo group.

Explanation

The compound is utilized in the pharmaceutical industry due to its potential biological activities, such as reducing inflammation and fighting fungal infections.

Explanation

The compound's unique stereochemistry makes it a valuable compound for studying and developing new drugs, as the spatial arrangement of atoms can significantly affect the compound's biological activity and efficacy.

Stereoisomer

Yes

Hydrogen atoms

6

Oxygen atoms

1

Pharmaceutical use

Anti-inflammatory and antifungal properties

Importance in drug research and development

Specific stereochemistry

Upstream product

• 58-85-5 (+/-)-biotin 
• 76335-62-1 5-[(3aR)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid 
• 3304-81-2 5-(2-oxo-2,3-dihydro-1H-thieno[3,4-d]imidazol-4-yl)-pentanoic acid 
• 75-44-5 phosgene 
• 3737-34-6 cis-3,4-diamino-2-tetrahydrothiophene valeric acid 
• 608-16-2 (+/-)-biotin methyl ester 
• 59851-15-9 (5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocin-3-yl)-carbamic acid methyl ester 
• 64820-06-0 5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester 
• 80615-61-8 5-((2S,3S,4R)-3,4-Bis-benzoylamino-tetrahydro-thiophen-2-yl)-pentanoic acid methyl ester 
• 73510-81-3 (εRS,4SR,5SR)-ε-Methylsulfonyloxy-5-methylsulfonyloxymethyl-2-oxo-4-imidazolidincapronsaeure-methylester 
• 58522-80-8 2-oxo-2,3-dihydro-4-(δ-methoxycarbonylbutyl)-1H-thieno<3,4-d>imidazole 
• 27051-47-4 ethyl ester of N,N'-diacetyl-α-keto-α'-acetylthiodehydrodesthiobiotin 
• 73520-47-5 (1r,10c)-3-Oxa-11,13-diazabicyclo<8.3.0>tridecan-4,9,12-trion 
• 65023-61-2 (εRS,4SR,5SR)-ε-Hydroxy-5-hydroxymethyl-2-oxo-4-imidazolidincapronsaeure-methylester 

Downstream Products

• 58-85-5 biotin 
• 58-85-5 vitamin H 
• 608-16-2 (+/-)-biotin methyl ester 
• 133643-39-7 5-((3aS,6R,6aR)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid (3-phenyl-propyl)-amide 
• 1233353-79-1 2,10-dimethoxy-9-(phenylsulfonyloxy)-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinolin-3-yl 5-((5S,1R,2R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl)pentanoate 
• 1429397-27-2 2-(4-((6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)piperazin-1-yl)-2-oxoethyl 5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate 
• 1374658-86-2 N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-5-[(4S)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide 
• 533-48-2 desthiobiotin 

Relevant articles and documents

A novel synthetic strategy for the stereospecific total synthesis of (±)-biotin

A concise and efficient TEA-mediated desymmetrization of meso-thioanhydride 6 with 5-ethoxy-5-oxopentylzinc bromine has been developed, which affords a convenient strategy for the stereospecific total synthesis of (±)-biotin 1.

A total synthesis of (+/-)-biotin

A total synthesis of (+/-)-biotin 1 based on the photochemical cycloaddition raection of 1,3-diacetylimidazolin-2-one 2 with 3,4-dihydro-2-methoxy-2H-pyran 3 is described.The photoadduct 4 was converted into the lactone 6, which bears the complete carbon framework and all the requisite stereochemical features, via hydrolysis, Wittig olefination, and catalytic hydrogenation to the cyclobutanol 5 followed by oxidative rearrangement.Subsequent conversion of the lactone to (+/-)-biotin followed from literature precedent (5).

A new synthesis of biotin

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