132352-48-8

Upstream product

• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 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 

Downstream Products

• 132352-49-9 ethyl (E)-3-((4S,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 224636-37-7 (2S,3S,4Z)-1-p-methoxybenzyloxy-2,3-isopropylidenedioxydodeca-4-ene 
• 132352-47-7 (4S,5S)-4-(3-hydroxy-1E-propenyl)-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 
• 132352-67-1 (4S,5S)-4-<(1R)-1-hydroxy-2-propynyl>-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxolane 
• 129083-15-4 (2S-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropylidenepropyl)oxiranemethanol 
• 129083-15-4 (2R-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropylidenepropyl)oxiranemethanol 
• 132352-59-1 (2R-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropyledinepropyl)oxiranemethylchloride 
• 132352-59-1 (2S-trans)-3-(3-p-methoxybenzyloxymethyl-1S,2S-O-isopropyledinepropyl)oxiranemethylchloride 
• 1313511-79-3 tert-butyl(((S,E)-6-((4S,5S)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhex-5-en-1-yl)oxy)diphenylsilane 
• 1199807-70-9 ((4S,5S)-5-((S,E)-6-((tert-butyldiphenylsilyl)oxy)-4-methylhex-1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 1199807-71-0 tert-butyl(((S,E)-6-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-methylhex-5-en-1-yl)oxy)diphenylsilane 
• 1259066-62-0 C₁₉H₂₆O₆ 
• 1259066-60-8 C₁₉H₂₆O₆ 

Relevant academic research and scientific papers

Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

The convergent total synthesis of naturally occurring paecilomycin C is described here for the first time. Asymmetric Brown allylation, E-selective cross metathesis, and a biomimetic carboxylate assisted intramolecular nucleophilic ring opening of an epoxide were employed to access the enantiopure γ-lactone framework of the natural product. Late stage E-selective Julia-Kocienski olefination was then employed to furnish the natural product in an efficient way.

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.

A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a

A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a has been achieved by using Yamaguchi esterification, Julia-Kocienski olefination, organocatalytic α-oxidation, and ring-closing metathesis reaction as key bond-forming 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.

Synthesis and biological activities of reveromycin A and spirofungin A derivatives

Various derivatives of reveromycin A, an inhibitor of eukaryotic cell growth, and spirofungin A, focusing on the 5S hydroxyl group and C18 hemisuccinyl group, were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and

Stereoselective total synthesis of (3R,8S)-falcarindiol, a common polyacetylenic compound from umbellifers

The first stereoselective total synthesis of (3R,8S)-falcarindiol (1) from L-tartaric acid and D-xylose is reported, via the Cadiot-Chodkiczwicz reaction, to couple 1-bromoalkyne (2) with 3(R)-(tert-butyldiphenylsilyloxy)- 1-penten-4-yne (3).

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).