70377-89-8

Basic information

• Product Name: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)- (9CI)
• Synonyms: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)- (9CI)
• CAS NO: 70377-89-8
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.1412
• Product Categories: ALDEHYDE
• Mol File: 70377-89-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)- (9CI)(70377-89-8)
• EPA Substance Registry System: 1,3-Dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)- (9CI)(70377-89-8)

Safety Data

• Hazardous Substances Data: 70377-89-8(Hazardous Substances Data)

Usage

Explanation

Different sources of media describe the Explanation of 70377-89-8 differently. You can refer to the following data:
1. The IUPAC name provides a standardized way to name chemical compounds. It includes the stereochemistry (2R,4R,5R), the functional groups (hydroxy, carboxaldehyde), and the core structure (1,3-dioxane).
2. The compound is derived from 1,3-dioxane, which is a six-membered ring containing two oxygen atoms. It has a hydroxyl (-OH) group and a carboxaldehyde (-CHO) functional group attached to the ring.
3. The stereochemistry indicates the orientation of the substituents on the carbon atoms. In this case, the hydroxyl group is attached to the 5th carbon (C5), the methyl group is attached to the 2nd carbon (C2), and the carboxaldehyde group is attached to the 4th carbon (C4). The (2R,4R,5R) notation specifies the clockwise arrangement of these substituents when viewed from the perspective of the hydrogen atom on the chiral carbon.
4. The hydroxyl group is a polar covalent bond between oxygen and hydrogen, while the carboxaldehyde group is a combination of a carbonyl (C=O) and an aldehyde (-CHO) functional group. These functional groups contribute to the compound's reactivity and properties.
5. Due to its unique structure and functional groups, 1,3-dioxane-4-carboxaldehyde, 5-hydroxy-2-methyl-, (2R,4R,5R)(9CI) is used as a building block in the synthesis of various biologically active molecules and pharmaceutical drug candidates.
6. The presence of the hydroxyl and carboxaldehyde functional groups makes this compound a versatile building block for the synthesis of complex molecules. These functional groups can participate in various chemical reactions, such as oxidation, reduction, and condensation, allowing for the creation of a wide range of compounds.

Structure

1,3-Dioxane derivative with a hydroxyl group and a carboxaldehyde functional group

Stereochemistry

(2R,4R,5R)

Functional Groups

Hydroxyl (-OH) and Carboxaldehyde (-CHO)

Application

Organic synthesis and pharmaceutical research

Reactivity

Valuable building block for synthesis

Upstream product

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• 13224-97-0 (1’R)-(-)-4,6-O-ethylidene-D-glucose 
• 18465-50-4 4,6-O-ethylidene-D-glucopyranose 

Downstream Products

• 1057964-92-7 3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-allonamide 
• 1030598-17-4 3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-mannonamide 
• 1030598-09-4 2,3-anhydro-N,N-dibenzyl-5-O-benzyl-4,6-O-ethylidene-D-altro-hexonamide 
• 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 
• 103670-22-0 (1R)-2,4-O-Etylidene-1,3-di-O-(4-nitrobenzoyl)-1-C-(dimethoxyphosphoryl)-D-erythritol 
• 103670-21-9 (1S)-2,4-O-Ethylidene-1,3-di-O-(4-nitrobenzoyl)-1-C-(dimethoxyphosphoryl)-D-erythritol 
• 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 
• 73466-12-3 Leukotriene A₄ methyl ester 

Relevant articles and documents

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.

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.

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).