14758-37-3

Usage

Molecular structure

2-(methylsulfanyl)-1,3-dithiane consists of a dithiane ring (a six-membered ring with two sulfur atoms) with a methylsulfanyl group (a methyl group attached to a sulfur atom) at position 2.

Functional groups

The dithiane ring and the methylsulfanyl group are the two main functional groups in 2-(methylsulfanyl)-1,3-dithiane.

Physical properties

The specific physical properties of 2-(methylsulfanyl)-1,3-dithiane are not provided in the material.

Uses

2-(methylsulfanyl)-1,3-dithiane is commonly used as a building block in organic synthesis, particularly in the preparation of heterocyclic compounds.

Protective group

The presence of the dithiane group makes 2-(methylsulfanyl)-1,3-dithiane a useful protective group for aldehydes and ketones, allowing for selective manipulation of these functional groups in complex molecule synthesis.

Reactivity

2-(methylsulfanyl)-1,3-dithiane can be used as a nucleophile in various reactions, making it a versatile reagent in organic chemistry.

Importance

2-(methylsulfanyl)-1,3-dithiane is an important and widely used compound in the field of chemical synthesis.

Upstream product

• 505-23-7 1,3 dithiane 
• 4973-66-4 methyl thiotosylate 
• 624-92-0 Dimethyldisulphide 
• 39141-54-3 2,2-bis(methylthio)-1,3-dithiane 
• 36049-90-8 2-lithio-1,3-dithiane 

Downstream Products

• 129225-91-8 2-methylthio-2-(3-phenylpropyl)-1,3-dithian 

Relevant academic research and scientific papers

A convenient high yield synthesis of functional methacrylates via dethioacetalization. Synthesis of methacrylate S,S-acetal derivatives as intermediates

We describe a selective and efficient synthesis of a whole new class of functional methacrylates starting from S,S-acetals. Carbonyl compounds were regenerated from corresponding S,S-acetaIs using mercury (II) salts. According to this method, methacrylic

Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures

Enantioselective sulphoxidation of a wide range of 2-substituted-1,3-diathianes has been carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide deriva

Compositions of retinoids substituted with a dithiane ring, their use, and process for preparing the compounds

The invention relates to a stereospecific derivative of formula: STR1 in which R is hydrogen or a C 1 -C 4 thioalkyl. The invention also relates to the use of these compounds for the manufacture of stereospecific retinal or retinoic acid, as well as to a process for preparing the retinoids of formula (I). The invention finally relates to a cosmetic or pharmaceutcial composition which contains at least one compound of formula (I) in a suitable vehicle; the pharmaceutical composition according to the invention may be used for treating dermatological, rheumatic, respiratory or ophthalmological conditions.

Propenals substituted with a dithiane ring and processes for the preparation of these propenals

Propenals of formula: STR1 in which formula R is H or a C1 -C4 thioalkyl radical, the dithiane ring being at the cis position in relation to the aldehyde function when R is H and at the trans position when R is a thioalkyl radical. The invention also relates to two processes for the preparation of these propenals.

Reactions of δ-valerolactone with lithio trithio-orthoformates

δ-valerolactone (3), on treatment with tris(methylthio)methyllithium (7) followed by weakly acidic aqueous work-up, gave a tautomeric mixture of 1,1-bis(methylthio)-6-hydroxy-2-hexanone (8a) and tetrahydro-2-bis(methylthio)methyl-2-pyranol (8b).Under analogous conditions 3 reacted with tris(phenylthio)methyllithium (10) to form tetrahydro-3-(phenylthiocarbonyl)-2-pyranone (11).With 2-(methylthio)-1,3-dithian-2-yllithium (16) it gave a tautomeric mixture of 2-(5-hydroxy-1-oxopentyl)-2-(methylthio)-1,3-dithiane (17a) and 2-(tetrahydro-2-hydroxy-2-pyranyl)-2-(methylthio)-1,3-dithiane (17b).Treatment of 17 with methanol in the presence of acidic ion-exchange resin gave a mixture of 2-(5,6-dihydro-3-(methylthio)-2(4H)-pyranyl-1,3-dithiane (20), 2-(tetrahydro-2-methoxy-2-pyranyl)-1,3-dithiane (21), and 2-(tetrahydro-2-methoxy-(4-methylthio)-2-pyranyl)-1,3-dithiane (22).Similar treatment of 20 gave a mixture of 20, 21, and 22.Compound 21 was synthesized independently by similar treatment of 2-(tetrahydro-2-hydroxy-2-pyranyl)-1,3-dithiane (23).The origins of the anomalous products are discussed briefly.It is concluded that because of these anomalies the preparation of tetrahydro-2-hydroxypyran-2-carboxylic acid acetals and related glycosides via trithio-orthoformate derivatives can encounter difficulties, although dithioacetales may serve this purpose. Key words: 1,3-dithianes, α-hydroxy acids, δ-lactones, trithio-orthoformates.

Synthesis of E Functionalized Prenyl Orthothioesters

A stereospecific route to (E)-3-2-methylpropenal 5 and to (E)-3-(4-methylthio-1,3-dithiane-2-yl)-2-methylpropenal 7 is described.

STUDY OF THE ANOMERIC EFFECT IN 2-SUBSTITUTED 1,3-DITHIANES

The conformational analysis of several 2-substituted 1,3-dithianes made possible the evaluation of S-C-Y anomeric interactions, where Y=SCH3,SC6H5,CO2CH3,COC6H5,CO2H and N(CH3)2.The relative magnitude of the effects observed for these groups odithiane(Y)-ΔGocyclohexane(Y)> can be explained in terms of the combined influence of dipole/dipole and two-electron stabilizing interactions (stereoelectronic effect).