81997-75-3

Basic information

• Product Name: (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate
• Synonyms: (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate
• CAS NO: 81997-75-3
• Molecular Weight: 214.262
• Mol File: 81997-75-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate(81997-75-3)
• EPA Substance Registry System: (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate(81997-75-3)

Safety Data

• Hazardous Substances Data: 81997-75-3(Hazardous Substances Data)

Upstream product

• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 535-11-5 Ethyl 2-bromopropionate 
• 2985-33-3 monoethyl methylmalonate 

Downstream Products

• 93635-76-8 (2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester 
• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 425427-13-0 (3R,4R,4'S)-2-N-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methyl-1,2-isoxazolidin-5-one 
• 108404-54-2 (3S,4S)-5-benzyloxy-4-hydroxy-3-isopropenylpentanoic acid lactone 
• 108404-44-0 (3R,4S)-5-benzyloxy-4-hydroxy-3-isopropenylpentanoic acid lactone 
• 108404-45-1 (3R,4S)-5-benzyloxy-3-(1-chloro-1-1-methylethyl)-4-hydroxypentanoic acid lactone 
• 108404-47-3 (1S,3R)-3-(2-benzyloxy-1-hydroxyethyl)-2,2-dimethylcyclopropanecarboxylic acid lactone 
• 93635-77-9 C₂₇H₂₂O₈ 
• 219926-62-2 (4S)-2,2-Dimethyl-4-[(Z)-2-methyl-3-phenylsulfonylprop-1-enyl]-1,3-dioxolane 
• 219926-65-5 (2E,4E)-5-Benzenesulfonyl-4-methyl-penta-2,4-dien-1-ol 
• 219926-66-6 (2E,4Z)-5-Benzenesulfonyl-4-methyl-penta-2,4-dien-1-ol 
• 93636-26-1 ethyl 4,5-O-isopropylidene-2-C-methyl-D-xylonate 

Relevant articles and documents

The Knoevenagel-Doebner reaction in the synthesis of branched-chain sugar derivatives

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A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-methylbutanoate, and (+)-lavandulyl senecioate through orthoester johnson-claisen rearrangement

An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. Copyright

Selective conjugate addition of nitromethane to enoates derived from D-mannitol and L-tartaric acid

The conjugate addition of nitromethane to enoates prepared from D-(+)-mannitol, substituted at the α-position by a methyl or a benzyl group, was investigated. While excellent syn-selectivity (d.e. >90%) was obtained from α-benzyl enoates (used as a mixture of epimers, E/Z=1.8:1), for α-methyl enoates the selectivity depended on the stereochemistry of the double bond in the acceptor (d.e. >90% for the (Z)-enoate and 50% for the (E)-enoate). In all cases, a mixture of epimers was formed at the newly generated stereocenter at the α-position. The epimeric syn-adducts were transformed into the corresponding pure α,β,γ-trisubstituted γ-butyrolactones by cyclization in acid medium followed by epimerization of the stereocenter at the α-position in DBU/CH2Cl2. When enoates derived from L-tartaric acid were used as acceptors, syn-selective conjugate additions were also observed (d.e. >90% for the (Z)-isomer and 50% for the (E)-isomer). The configuration at the newly generated stereogenic centers were assigned based on X-ray analyses, 1H-1H coupling constants and NOE experiments in NMR spectroscopy.