124662-66-4

Upstream product

• 63952-83-0 (2S)-acetic acid 6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 41976-28-7 (5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one 
• 2873-29-2 D-glucal triacetate 
• 602326-63-6 (S)-2-(benzyloxymethyl)-3,6-dihydro-2H-pyran 
• 100-39-0 benzyl bromide 
• 172323-66-9 (S)-(-)-(3,6-Dihydro-2H-pyran-2-yl)methanol 
• 646058-48-2 6(S)-carboxymethyl-2-methoxy-5,6-dihydro-2H-pyran 
• 124662-61-9 (S)-5-Benzyloxy-4-hydroxy-1-pentyne 
• 124662-64-2 Methyl (S)-6-benzyloxy-5-tert-butyldimethylsiloxy-2-hexynoate 
• 124662-62-0 (S)-6-Benzyloxy-5-hydroxy-hex-2-ynoic acid 
• 124662-63-1 (S)-5-Benzyloxy-4-tert-butyldimethylsiloxy-1-pentyne 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 

Downstream Products

• 291506-89-3 (3R,5S)-6-benzyloxy-3,5-dihydroxyhexanoic acid isopropyl ester 
• 885666-75-1 (6S)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 
• 92757-18-1 (4R,6S)-6-(benzyloxy)methyl-4-hydroxy-tetrahydro-2-pyrone 
• 859844-06-7 (3aR,6S,7aR)-6-(benzyloxymethyl)-2,2-dimethyl-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4(6H)-one 
• 859844-05-6 (3R,4R,6S)-6-(benzyloxymethyl)-3,4-dihydroxytetrahydropyran-2-one 

Relevant academic research and scientific papers

Stereochemical course of the [4+2] cycloaddition of 1-methoxybuta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam. The formal synthesis of compactin and mevinolin

The chiral heterodienophile N-glyoxyloyl-(2R)-bornane-10,2-sultam 2, readily prepared from (2R)-bornane-10,2-sultam 1, was used in noncatalyzed atmospheric and high-pressure as well as in [Eu(fod)3]-catalyzed [4+2] cycloadditions with 1-methoxybuta-1,3-diene 3. All the [4+2] cycloadditions studied led to diastereoisomeric mixtures of 6-substituted derivatives of 2-methoxy-5,6-dihydro-2H-pyran 4-7. The extent of asymmetric induction in these reactions was established by 1H NMR analysis and the absolute configuration of the thermodynamically stable products 5 and 7 by X-ray analysis, and independently by chemical correlation. Stereochemical models for both noncatalyzed and [Eu(fod3]-promoted reactions are proposed. The [4+2] cycloadduct 5 was then effectively transformed into (4R)-hydroxy-(6S)-hydroxymethyltetrahydropyrone-2 12, a key synthon for the lactone moiety of compactin 10 and mevinolin 11.

Enantioselective Hetero-Diels-Alder reaction with glyoxylate catalyzed by chiral titanium complex: Asymmetric synthesis of the lactone portion of mevinolin and compactin

Asymmetric Diels-Alder reaction with methyl glyoxylate catalyzed by the chiral titanium complex 1 provides the dihydropyran carboxylate in high enantiomeric purity, which can be converted to the lactone portion of mevinolin or compactin.

Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol

The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting-group strategy led to the modification of this approach beginning with (±)-glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero-Diels-Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition into the corresponding enone synthon. Addition of a model alkyne provides support for the late-stage addition of a hindered alkyne to the caprolactam building block.

A concise and efficient synthesis of spiroketals - Application to the synthesis of SPIKET-P and a spiroketal from bactrocera species

We report the synthesis of spiroketals by sequence of enol ether synthesis and cyclization. The enol ethers were prepared from lactones by a Julia olefination reaction, and the starting chiral lactone was prepared from an industrial intermediate. This route is a concise and efficient way to synthesize naturally occurring and biologically interesting spiroketals. We used this sequence for the preparation of SPIKET-P and a spiroketal from Bactrocera species. Copyright

Synthesis of mono- and dihydroxylated furanoses, pyranoses, and an oxepanose for the preparation of natural product analogue libraries

Numerous biologically active natural products contain furanoses and pyranoses with mono- and dihydroxylated substituents. However, much of the structure-activity studies on such molecules is gathered on the aglycons without attention to the corresponding carbohydrate components. Consequently, there are few synthetic procedures that enable the rapid preparation of mono- and dihydroxyfuranoses and mono- and dihydroxypyranoses and no report for a 3,4-dihydroxyoxepanose. In this article we report the practical synthesis of orthogonally protected five-, six-, and seven-membered carbohydrate derivatives. The succinct manner in which these molecules were synthesized allows the rapid preparation of analogues aimed at discovering the role of ring size and individual hydroxyl moieties on the pyranose skeleton.

Highly chemoselective oxidation of 1,5-diols to δ-lactones with TEMPO/BAIB

The selective oxidative conversion of a variety of highly functionalized 1°,2°-1,5-diols into the corresponding δ-lactones has been effected simply and efficiently using a reagent system comprised of catalytic 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and

Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs

Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the correspondi

A versatile preparation of alpha,beta-unsaturated lactones from homoallylic alcohols.

[formula: see text] A new method for the synthesis of alpha,beta-unsaturated lactones from beta-acetoxy aldehydes by reaction with the lithium enolate of methyl acetate was developed. The reaction is relatively insensitive to structural changes in the ald

An improved dienophile-induced access to enantiopure 2,4-dideoxysugar lactones via hetero Diels-Alder reaction: Synthesis of the (+)-lactone moiety of compactin

Polystereocontrolled access to 4-type heterocycloadducts was consistently improved by using a new 4-oxy-substituted 1-oxabutadiene, methyl (E)-tert-butoxymethylenepyruvate (1c). Obtained in both enantiomeric forms with high diastereomerical purity, these adducts led to diprotected 2,4- dideoxyglucose 10 and -gluconolactone 12 in both L and D series in high yields. Epimerization of (-)-12 via intramolecular Mitsunobu inversion gave a straightforward access to the lactone moiety (+)-16 of compactin.

A Unified Procedure for Diastereo- and Enantiocontrolled Construction of Compactin Lactone and Calcitriol Enyne

A unified diastereo- and enantiocontrolled entry into compactin lactone, an essential structural moiety for the biological activity of compactin, and calcitriol enyne, an A-ring precursor of calcitriol, has been developed by use of the same stereocontrol