132352-49-9

Basic information

• Product Name: ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
• Synonyms: ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
• CAS NO: 132352-49-9
• Molecular Weight: 350.412
• Mol File: 132352-49-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate(132352-49-9)
• EPA Substance Registry System: ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate(132352-49-9)

Safety Data

• Hazardous Substances Data: 132352-49-9(Hazardous Substances Data)

Upstream product

• 118620-86-3 (2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol 
• 132352-48-8 4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 179548-99-3 (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene 
• 140-88-5 ethyl acrylate 
• 121289-23-4 p-methoxybenzyloxyacetaldehyde 
• 1313191-18-2 (2S,3S)-1-(4-methoxybenzyloxy)-3-(methoxymethoxy)pent-4-en-2-ol 
• 2746-25-0 p-Methoxybenzyl bromide 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 116-11-0 2-Methoxypropene 
• 531515-01-2 (E)-ethyl (4S,5S)-4,5-dihydroxy-6-(4-methoxybenzyloxy)-hex-2-enoate 

Downstream Products

• 132352-47-7 (4S,5S)-4-(3-hydroxy-1E-propenyl)-5-(p-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 132352-47-7 (E)-3-((4S,5S)-5-((4-ethoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 72458-46-9 N-benzyl-1-deoxynojirimycin 
• 214342-00-4 (3aS,6R,7R,7aS)-5-Benzyl-2,2-dimethyl-6-vinyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 
• 214342-01-5 (3aS,6R,7R,7aS)-5-Benzyl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 
• 214342-03-7 (1R,2R)-2-Benzylamino-1-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol 
• 129083-15-4 {(2S,3R)-3-[(4R,5S)-5-(4-Methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-methanol 
• 160836-02-2 (E)-(2S,3S)-6-Benzyloxy-1-(4-methoxy-benzyloxy)-hex-4-ene-2,3-diol 
• 160836-00-0 (E)-(2S,3S)-6-Benzyloxy-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-hex-4-en-1-ol 
• 1026712-54-8 (E)-(2R,3S)-6-Benzyloxy-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-hex-4-enal 
• 142138-46-3 (E)-(3R,4S,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-oct-6-enoic acid ethyl ester 
• 142138-40-7 (E)-(4R,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-oct-6-enoic acid ethyl ester 
• 132352-67-1 (4S,5S)-4-<(1S)-1-hydroxy-2-propynyl>-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxolane 

Relevant articles and documents

Chirality transfers through sequential sigmatropic rearrangements of allylic vicinal diols: Development and application to total synthesis of (-)-kainic acid

A detailed description is presented of two sequential sigmatropic rearrangements starting from enantiopure allylic vicinal diols. Starting from the same allylic diol, the sequential Claisen/Claisen rearrangement can install two identical functional groups in a one-pot reaction, whereas, the sequential Claisen/Overman rearrangement can introduce two different functional groups, both occurring without protecting group manipulation. Both sequential reactions proceeded with complete stereoselectivity, which was easily predictable by the judicious choice of two factors regarding the allylic diols: (1) the stereochemistry of the hydroxy groups and (2) the geometry of the olefin. To demonstrate this sequential rearrangement methodology, we accomplished the total synthesis of (-)-kainic acid, whose three contiguous stereocenters were completely established by three chirality transfer reactions (SN2' and sequential Claisen/Overman reactions) of flexible acyclic intermediates derived from D-arabinose. A detailed investigation is described of two sequential sigmatropic rearrangements from allylic diols. Starting from the same allylic diol, either two identical functional groups (Claisen/Claisen) or two different functional groups (Claisen/Overman) were diastereoselectively installed. The reaction was successfully applied to the total synthesis of (-)-kainic acid.

Novel sequential sigmatropic rearrangements of allylic diols: Application to the total synthesis of ( - )-kainic acid

Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of ( - )-kainic acid.

Conformational Diagnosis of Diethyl (4S,5S)-4,5-Bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate Based on the Stereochemical Outcomes of Representative Reactions As Compared with Those of Its 4,5-O-Isopropylidene Derivatives and on a Dichroic Exciton C

In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, ha