81703-93-7

Basic information

• Product Name: METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE
• Synonyms: (S)-METHYL-4,5-ISOPROPYLIDENEPENT-2-ENOATE;METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE;methyl (S)-(+)-3-(2,2-dimethyl-1,3-dioxolan-4-yl);methyl (E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS NO: 81703-93-7
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.21
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 81703-93-7.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 260.961°C at 760 mmHg
• Flash Point: 204 °F
• Appearance: /
• Density: 1.079 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• CAS DataBase Reference: METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE(81703-93-7)
• EPA Substance Registry System: METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE(81703-93-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 81703-93-7(Hazardous Substances Data)

Usage

General Description

Methyl (S)-(+)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate is a chemical compound with the molecular formula C9H14O4. It is a colorless liquid that is commonly used in the production of pharmaceuticals, agrochemicals, and fragrances. METHYL (S)-(+)-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-TRANS-2-PROPENOATE is known for its ability to act as a chiral building block in the synthesis of various organic compounds. It is also used as a flavoring agent in the food industry. Additionally, it is a versatile intermediate in organic synthesis and is valued for its high purity and enantiomeric excess. Overall, Methyl (S)-(+)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate is an important chemical in the pharmaceutical and fragrance industries, as well as in organic synthesis.

InChI:InChI=1/C9H14O4/c1-9(2)12-6-7(13-9)4-5-8(10)11-3/h4-5,7H,6H2,1-3H3/b5-4+/t7-/m0/s1

Upstream product

• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 5927-18-4 trimethyl phosphonoacetate 
• 69-65-8 mannitol 
• 77-76-9 2,2-dimethoxy-propane 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 72946-10-2 diisopropyl (methoxycarbonylmethyl)phosphonate 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 453-17-8 D-Glyceraldehyde 
• 36326-38-2 3-<(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>prop-2-enoic acid ethyl ester 

Downstream Products

• 141985-55-9 methyl (1RS,2RS)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-4-cyclohexen-1-ylcarboxylate 
• 357675-06-0 methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 87408-22-8 (R)-N-benzyl-4-<(methoxycarbonyl)methyl>-2-azetidinone 
• 87408-20-6 (R)-1-Benzyl-4-vinyl-azetidin-2-one 
• 87417-37-6 (R)-3-(Benzyl-benzyloxycarbonyl-amino)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 
• 87408-23-9 (3R,4S)-3-(Benzyl-benzyloxycarbonyl-amino)-4,5-dihydroxy-pentanoic acid methyl ester 
• 87408-28-4 (S)-3-(Benzyl-benzyloxycarbonyl-amino)-pentanedioic acid monomethyl ester 
• 87408-25-1 (E)-(R)-3-(Benzyl-benzyloxycarbonyl-amino)-5-methoxy-pent-4-enoic acid methyl ester 
• 87408-19-3 Methanesulfonic acid (S)-1-((R)-1-benzyl-4-oxo-azetidin-2-yl)-2-methanesulfonyloxy-ethyl ester 
• 87408-27-3 (S)-3-(Benzyl-benzyloxycarbonyl-amino)-5-oxo-pentanoic acid methyl ester 

Relevant articles and documents

An approach to the carbon backbone of bielschowskysin, part 1: Photocyclization strategy

Several macrocyclization reaction attempts of highly advanced precursors toward a total synthesis of marine diterpene bielschowskysin are disclosed. Biomimetic [2+2]-photocyclization reactions were applied to construct the cyclobutane core in these intermediates, which could be accessed along scalable high-yielding reaction sequences from cheap enantiopure starting-materials. Asymmetric syntheses of various highly functionalized intermediates toward the total synthesis of bielschowskysin (1) are described. In particular a biomimetic [2+2]-photocycloaddition reaction strategy, forming the cyclobutane core, was followed by various macrocyclization reactions attempts. Copyright

Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: Potent inhibitors of heat shock protein 90

A full account of an asymmetric synthesis of reblastatin (1) and the first total synthesis of autolytimycin (2) and related structural compounds is described. The syntheses expand the utility of a highly regio- and diastereoselective hydrometalation aldehyde addition sequence to assemble the fully functionalized ansa chain of the natural products. Also documented is an intramolecular copper-mediated amidation reaction to close the 19-membered macrolactams. The amidation reaction was also employed for the generation of structural derivatives (6-9) of phenolic ansamycins. Ansamycin natural products and selected structural analogues were evaluated in a competitive binding assay to breast cancer cell lysate and a cytotoxicity assay. Both reblastatin (1) and autolytimycin (2) were shown to bind the heat shock protein 90 with enhanced binding activity (～25 nM) than 17-allylamino-17-demethoxygeldanamycin (17-AAG, 4), a geldanamycin (3) derivative currently under evaluation for treatment of cancer (～100 nM).

Process for preparing alpha, beta - unsaturated ester

A process for preparing an α,β-unsaturated ester of the compound (4), wherein R7 and R8 are the same or different and hydrogen atom, C1-6alkyl group or phenyl group, which comprises oxidizing a glycerol derivative (2), wherein R7 and R8 are the same as defined above, in the presence of a nitroxyl radical compound and a co-oxidant to prepare a glyceraldehyde and then reacting the compound with a phosphonoacetic acid alkyl ester or a (triphenylphosphoranylidene)acetic acid alkyl ester to give the compound (4).