183387-39-5

Basic information

• Product Name: 2(3H)-Furanone,dihydro-3-hydroxy-4-methyl-5-(1-methylethyl)-,(3S,4S,5R)-(9CI)
• Synonyms: 2(3H)-Furanone,dihydro-3-hydroxy-4-methyl-5-(1-methylethyl)-,(3S,4S,5R)-(9CI)
• CAS NO: 183387-39-5
• Molecular Formula: C8H14O3
• Molecular Weight: 0
• Product Categories: ISOPROPYL
• Mol File: 183387-39-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(3H)-Furanone,dihydro-3-hydroxy-4-methyl-5-(1-methylethyl)-,(3S,4S,5R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone,dihydro-3-hydroxy-4-methyl-5-(1-methylethyl)-,(3S,4S,5R)-(9CI)(183387-39-5)
• EPA Substance Registry System: 2(3H)-Furanone,dihydro-3-hydroxy-4-methyl-5-(1-methylethyl)-,(3S,4S,5R)-(9CI)(183387-39-5)

Safety Data

• Hazardous Substances Data: 183387-39-5(Hazardous Substances Data)

Upstream product

• 381246-76-0 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexanoic acid methyl ester 
• 381246-75-9 (E)-(4R)-4-benzyloxymethoxy-5-methylhex-2-enoic acid methyl ester 
• 381247-06-9 (R)-2-Benzyloxymethoxy-3-methyl-butan-1-ol 
• 381247-05-8 (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester 
• 906534-74-5 (R)-2-Benzyloxymethoxy-3-methyl-butyraldehyde 
• 90244-32-9 (R)-methyl 2-hydroxy-3-methylbutanoate 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 640-68-6 D-Val-OH 
• 183201-71-0 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 
• 56767-19-2 5-isopropylfuran-2(5H)-one 
• 120313-18-0 (R^*,S^*)-4-hydroxy-3,5-dimethyl-2-oxo-N,N-diethylhexanamide 
• 160741-81-1 (3S,4R,5R)-3-Hydroxy-5-isopropyl-4-methyl-dihydro-furan-2-one 
• 85710-97-0 (4R*,5R*)-4,5-dihydro-5-isopropyl-4-methyl-2(3H)-furanone 
• 120313-28-2 (2S,3R,4S)-2,4-Dihydroxy-3,5-dimethyl-hexanoic acid diethylamide 

Downstream Products

• 106470-99-9 3(R^*)-hydroxy-4(S^*)-methyl-5(R^*)-isopropyltetrahydrofuran-2-one 

Relevant articles and documents

Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors

The macrolide bafilomycin A1 was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A1 via a conventional carbodiimide-mediated Keck-type macrolactonization.

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The first examples of nondehydrative, kinetic aldol condensations of 3-methyl and 3-phenoxy-2-oxo (tertiary) carboxamides are reported.Addition of hydride or methyl Grignard nucleophiles to the aldol products produced diol or monoprotected triol amides with high stereoselectivity in some cases.One of these compounds was elaborated to the methyl glycosides of (-)-cladinose and (+)-mycarose.