132352-49-9

Upstream product

• 132352-48-8 4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose 
• 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 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 118620-86-3 (2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-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

• 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 
• 1313191-19-3 ethyl 3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate 
• 132352-59-1 (2S-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropyledinepropyl)oxiranemethylchloride 
• 132352-59-1 (2R-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropyledinepropyl)oxiranemethylchloride 
• 129083-15-4 (2R-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropylidenepropyl)oxiranemethanol 
• 129083-15-4 (2S-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropylidenepropyl)oxiranemethanol 
• 132352-67-1 (4S,5S)-4-<(1R)-1-hydroxy-2-propynyl>-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxolane 
• 132352-67-1 (4S,5S)-4-<(1S)-1-hydroxy-2-propynyl>-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxolane 
• 142138-40-7 (E)-(4R,5S)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-oct-6-enoic acid ethyl ester 

Relevant academic research and scientific papers

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.

Stereoselective total synthesis of (+)-sapinofuranone B

Two approaches for the total synthesis of (+)-sapinofuranone B have been described. The first strategy utilizes the methodology developed earlier in our group to get the chiral propargyl alcohol and the second strategy involves generation of threo-1,2-diol derivative by diastereoselective and enantioselective addition of [(Z)-γ-methoxymethoxyallyl] diisopinocampheylborane onto aldehyde and cross metathesis as the key steps.

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.

Asymmetric synthesis of (+)-1-deoxynojirimycin

An asymmetric synthesis of (+)-1-deoxynojirimycin (1) in 14 steps starting from diene (5) is described. The key transformations in the sequence are a sharpless dihydroxylation and epoxidation followed by a regio- and stereoselective aminolysis of vinyl epoxide 11 to give piperidine 12.

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

AN EFFECTIVE, PRACTICAL METHOD FOR THE SYNTHESIS OF CHIRAL PROPARGYL ALCOHOLS

The preparation of chiral propargyl alcohols (2) is described by LiNH2 or LDA induced double elimination of chiral epoxychlorides (4), derived from their corresponding epoxyalcohols (3) which are available easily by Sharpless asymmetric epoxidation of the primary allyl alcohols.Whereas, use of stoichiometric amount of base on 4 provides chirally enriched trans-1-chlorovinyl alcohols (14).