315216-23-0

Usage

Stereochemistry

(4S,5S)-

Explanation

This notation indicates the stereochemistry of the compound, specifically the configuration of the chiral centers at the 4th and 5th positions. The "S" denotes that the substituents are in a specific arrangement, which is important for the compound's properties and reactivity.

Explanation

Isomers are compounds with the same molecular formula but different arrangements of atoms in space. 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (4S,5S)- (9CI) is a specific stereoisomer of the 1,3-dioxane molecule, which means it has the same molecular formula but a different spatial arrangement of atoms.

Explanation

The compound contains a carboxaldehyde (C=O), a hydroxyl (-OH), and a methyl (-CH3) functional groups, which contribute to its chemical properties and reactivity.

Explanation

The compound is solid at room temperature, which means it has a stable, rigid structure that does not easily change shape or flow.

Explanation

The compound can dissolve in organic solvents, such as alcohols, ethers, and hydrocarbons, due to its nonpolar nature and the presence of hydrocarbon groups in its structure.

Explanation

The compound should be handled with care due to its potential hazards. It may be harmful if ingested or inhaled, and could cause irritation to the skin and eyes. Proper safety measures, such as wearing gloves and using eye protection, should be taken when working with 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (4S,5S)- (9CI).

Isomer

Stereochemically-defined isomer of 1,3-dioxane

Functional Groups

Carboxaldehyde, hydroxyl, and methyl groups

Physical State

Solid at room temperature

Solubility

Soluble in organic solvents

Applications

Organic synthesis and pharmaceuticals

Safety Precautions

Potential hazards

Upstream product

• 18465-50-4 4,6-O-ethylidene-D-glucopyranose 
• 13224-97-0 (1’R)-(-)-4,6-O-ethylidene-D-glucose 
• 105453-33-6 4,6-O-ethylidene-D-glucose 
• 112246-57-8 O⁴,O⁶-((S)-ethylidene)-L-glucose 
• 13403-24-2 4,6-(Ethylidenedioxy)-D-glucopyranose 

Downstream Products

• 33805-14-0 (O³,O⁵-(R)-ethane-1,1-diyl-D-erythro-2-deoxy-pent-1-enitol-1-yl)-phosphonic acid lactone (Ξ)-phenyl ester 
• 29810-04-6 endo-2,3-O-ethylidene-β-D-erythrofuranose 
• 77489-43-1 exo-1,2-O-ethylidene-α-D-erythrofuranose 
• 77519-84-7 exo-2,3-O-ethylidene-β-D-erythrofuranose 
• 73958-00-6 (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester 
• 73957-99-0 (-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester 
• 70369-46-9 (2R,4S,5R)-4-hydroxymethyl-2-methyl-1,3-dioxan-5-ol 
• 1030598-21-0 2,4-di-O-acetyl-3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-allonamide 
• 1030598-19-6 2,4-di-O-acetyl-3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-mannonamide 

Relevant academic research and scientific papers

Stereoselectivity in the Ortho Ester Claisen Rearrangements of the E and Z Isomers of γ-(1,3-Dioxan-4-yl)allyl Alcohols

The E and Z isomers of (2R,4S,5R)-5-hydroxy-4-(3-hydroxy-1-propenyl)-2-methyl-1,3-dioxane (3Z and 3E), which were derived from 4,6-O-ethylidene-D-glucose (1), and their 5-O-tert-butyldimethylsilyl derivatives (5Z) and (5E) served as substrates for Claisen rearrangements with triethyl orthoacetate.The rearrangement employing 5Z proceeds with moderate to high levels of diastereoselectivity.The chemically determined stereochemical assignments of the newly introduced stereogenic centers in the rearrangement products reveal that the diastereomer with an R configuration isthe major rearrangement product.The results of the Claisen rearrangement of 5Z with triethyl orthopropionate are also described.

NOVEL DIOL COMPOUNDS SYNTHESIS AND ITS USE FOR FORMAL SYNTHESIS OF (2R, 3 S)-3-HYDROXYPIPECOLIC ACID

The patent discloses novel diol derivatives of general formula I, [Formula should be inserted here] A chiral pool process for the synthesis of the compound of formula I from D glucose. Further, it discloses a process for the synthesis of (2R, 3S)-3-hydroxypipecolic acid from D- glucose using chiral pool approach, wherein the D-glucose used is in enantiomerically pure form.

Synthesis of the fused polyether core of hemibrevetoxin B by two-directional ring-closing metathesis

(Chemical Equation Presented) The tetracyclic fused polyether core of the marine natural product hemibrevetoxin B has been prepared in an efficient manner by using a strategy in which ring-closing metathesis (RCM) reactions were employed for ring synthesi

Allelochemicals of the tropical weed Sphenoclea zeylanica

Nine plant growth inhibitors were isolated from the tropical weed Sphenoclea zeylanica, which shows allelopathic properties. Those compounds hitherto not reported from any plant source were the isomers of cyclic thiosulfinate, (1S,3R,4R)-(+)- and (1R,3R,4R)-(-)-4-hydroxy-3-hydroxymethyl-1,2-dithiolane-1-oxides, and (2R,3R,4R)-(-)- and (2S,3R,4R)-(+)-4-hydroxy-3-hydroxymethyl-1,2-dithiolane-2-oxides. These were named Zeylanoxide A, epi-zeylanoxide A, zeylanoxide B and epi-zeylanoxide B, respectively. The absolute configurations at C-3 and C-4 were elucidated by chemical synthesis of both enantiomers from L- and D-glucose. Two of the inhibitors were secologanic acid and secologanoside, and three other inhibitors were by known secoiridoid glucosides formed as artifacts during extraction with methanol. The cyclic thiosulfinates and secoiridoid glucosides completely inhibit the root growth of rice seedlings at 3.0 mM. While the specific activity of the inhibitors was not high, since they accumulated to circa 0.61% S. zeylanica by dry weight, this suggests that the inhibitors are nervertheless potent allelochemicals in this weed. (C) 2000 Elsevier Science Ltd.

Radical cyclization of oxime ethers derived from monosaccharides aiming at the synthesis of dysiherbaine and related stereoisomers

Stannyl radical-mediated cyclization of oxime ethers (6), (14), (22), and (29) derived from glucose and galactose afforded the cyclized aminosugar derivatives (7), (8), (15, 16 and 17), (23), (24), and (30, 31 and 32) which would serve as key intermediates for the synthesis of dysiherbaine and its isomers.

Total synthesis of fully acetylated N-acetylneuraminic acid (Neu5Ac), 2-deoxy-β-Neu5Ac, and 4-epi-2-deoxy-β-Neu5Ac from D-glucose

(equation presented) Sialic acid and its analogues have been synthesized using a salenCo(ll) complex catalyzed hetero Diels-Alder reaction and oxidative azidation (CAN/NaN3) of silyl enol ether as the key steps.

β-lactams from D-erythrose-derived imines: A convenient synthesis of 2,3-diamino-2,3-dideoxy-d-mannonic-acid derivatives

The D-manno-configured N-anisylated β-lactam 40, the β-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively. None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the β- lactam amino acid 43, besides its hydrolysis product 44. Reductive N- acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-β-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-β-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected β- lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).

Synthesis and biological activity of 4-methyl-3,5-dioxane derivatives as thromboxane A2 receptor antagonists

The synthesis and biological activity of novel 4-methyl-3,5-dioxane analogues are described. All compounds were produced through modification of the substituent formally corresponding to the ω-octenol side chain of thromboxane A2 (TXA2/su

Dioxalanones as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-Deoxy-D-Arabino-2-Heptulosonic acid (DAH) and 2-Keto-3-Deoxy-D-Gluconic acid (KDG)

Three biosynthetically significant α-keto acids KDO (7), DAH (8) and KDG (9) have been synthesised via 5-ylidene-1,3-dioxalan-4-one intermediates formed by Wittig reactions of protected monosaccharide-derived aldehydes with the Wittig reagent (3).

Enantiospecific syntheses of leukotrienes C4, D4 and E4 and [14,15-3H2]leukotriene E4 dimethyl ester

A 'chiral-pool' approach was employed to synthesize various leukotrienes (slow-reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S,S)-trans-epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D-araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S,R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting material. Elaboration of 9 into leukotriene A4 methyl ester (5) and the potassium salts of leukotrienes C4 (4a), D4 (4b), and E4 (4c) was accomplished by standard methods. These salts exhibited potent contractile activities in the in vitro guinea pig ileum assay. Reduction of 14,15-dehydroleukotriene A4 methyl ester (44) with tritium gas gave [14,15-3H2]-5 and subsequently the dimethyl ester of [14,15-3H2]leukotriene E4 having a high specific activity of 40 Ci/mmol.