84379-53-3

Usage

InChI:InChI=1/C11H16O4/c12-6-10(14)11(7-13)15-8-9-4-2-1-3-5-9/h1-5,10-14H,6-8H2/t10-,11-/m0/s1

Upstream product

• 116-11-0 2-Methoxypropene 
• 84379-51-1 2-O-benzyl-L-threitol 
• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 67-64-1 acetone 
• 100-39-0 benzyl bromide 
• 77-76-9 2,2-dimethoxy-propane 
• 866771-99-5 [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 
• 100906-45-4 (5S,6S)-6-(benzyloxy)-2,2-dimethyl-1,3-dioxepan-5-ol 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 100-52-7 benzaldehyde 
• 333788-78-6 (2S,3S)-2-Benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-butane-1,4-diol 
• 121357-96-8 methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 340699-28-7 ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 

Downstream Products

• 84379-60-2 2-O-benzyl-3,4-O-isopropylidene-1-O-octadecyl-L-threitol 
• 91282-44-9 (S)-4-((S)-1-Benzyloxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane 
• 177957-84-5 (2S,3S)-3-(O-benzyl)-4-[O-(p-methoxy)benzyl]-1,2,3,4-butanetetraol-1,2-di-O-acetonide 
• 499973-31-8 (2S,3S)-3-(O-benzyl)-4-[O-(p-methoxy)benzyl]-1,2,3,4-butanetetraol 
• 896729-93-4 C₃₃H₃₂O₇ 
• 1584709-81-8 C₂₆H₃₁ClN₂O₄ 
• 1584709-82-9 C₂₇H₃₄N₂O₄ 
• 1584709-84-1 C₂₆H₃₂N₂O₄ 
• 1584709-85-2 C₂₆H₃₀Cl₂N₂O₄ 
• 1584709-86-3 C₂₆H₃₁FN₂O₄ 
• 1584709-87-4 C₂₇H₃₄N₂O₅ 
• 1584709-72-7 (S)-3-(benzyloxy)-1-(4-chlorophenyl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-one 
• 1584709-74-9 (S)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(p-tolyl)propan-1-one 
• 1584709-76-1 (S)-3-(benzyloxy)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one 

Relevant academic research and scientific papers

Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues

A flexible synthetic approach to biologically active sphingoid base-like compounds with a 3-amino-1,2-diol framework was achieved through a [3,3]-sigmatropic rearrangement and late stage olefin cross-metathesis as the key transformations. The stereochemistry of the newly created stereogenic centre was assigned via a single crystal X-ray analysis of the (4S,5R)-5-(hydroxymethyl)-4-vinyloxazolidine-2-thione. In order to rationalise the observed stereoselectivity of the aza-Claisen rearrangement, DFT calculations were carried out. The targeted isomeric sphingoid bases were screened in vitro for anticancer activity on a panel of seven human malignant cell lines. Cell viability experiments revealed that C17-homologues are more active than their C12 congeners.

Synthesis of C1–C11 eribulin fragment and its diastereomeric analogues

A practical stereoselective synthesis of the central C1–C10 fragment of eribulin and its two diastereomeric analogues is developed. Our approach relied on the use of L-ascorbic acid as the starting material which allowed accessing a key intermediate with a syn diol moiety (C9 and C10 of eribulin) and a carboxylic ester group. A functionalized six membered lactone having several required hydroxyl groups was then obtained. In a number of steps, the lactone was converted to an intermediate for our key oxa-Michael reaction. A regio- and stereocontrolled intramolecular oxa-Michael reaction completed the synthesis of the C1–11 fragment having a trans-fused tetrahydropyrans with the exact stereochemistry of various hydroxyl groups, as in eribulin.

Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knieo on the occasion of his 70th birthday

Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group

Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation Dedicated to Associated Professor Ladislav Knie?o on the occasion of his 70th birthday

Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl l-tartrate and/or l-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group

Facile synthesis of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone

The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structu

Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy- α,β-unsaturated esters C via the int

Synthesis of (1R,2S)- and (1S,2S)-3-azido-1,2-dihydroxypropylphosphonates

An efficient synthesis of diastereomerically pure dimethyl (1R,2S)- and (1S,2S)-3-azido-1,2-dihydroxypropylphosphonates from L-ascorbic acid, via new chirons: (2S,3S)-4-azido-3-benzyloxy-1,2-O-isopropylidene-1,2-butanediol and (2S)-3-azido-2-benzyloxypropanal was elaborated.

The first total synthesis of (+)-rogioloxepane A

The first total synthesis of (+)-rogioloxepane A is described. The α,ω-trans-disubstituted oxepene skeleton was stereoselectively constructed via cyclization of the hydroxy epoxide promoted by the (Bu3Sn)2O/Zn(OTf)2 system. The proposed configurations of 6R and 13R were confirmed through this synthetic study.

Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered αβ-Unsaturated Esters: Stereoselective Synthesis of Optically Pure C-Furanosides

Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA.-). The DCA.- is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.

Total synthesis of an enantiomeric pair of FR980482. 2. Syntheses of the aromatic and the optically active aliphatic segments

The synthesis of the aromatic segment 4 was achieved starting from commercially available 5-hydroxyisophthalic acid (6) by utilizing Claisen rearrangement of 9, bromolactonization of 12, and modified Curtius rearrangement of 16 as the key steps. Furthermore, the optically active aliphatic segments 5 and ent-5 were synthesized in enantiomerically pure forms starting with natural (2R, 3R)- and unnatural (2S, 3S)-diethyl tartrate (7 and ent-7), respectively: The synthetic scheme features epoxide formation of 26, nucleophilic epoxide opening of 27 with an azide anion, reduction of the azide function in 33 to an amine, and formation of the N-protected 1,3-oxazolidine 35.