69977-56-6

Usage

2. Chemical Nature

Amino alcohol
3. Functional Groups: Contains an amino group (NH2), a hydroxyl group (OH), a methyl group (CH3), and a sulfur atom (S).
4. Role in Biosynthesis: Intermediate in the biosynthesis of methionine and coenzyme A.
5. Applications:
Used as a building block in pharmaceuticals and organic compound synthesis.
Versatile chemical for industrial and research purposes.
6. Structure: 2-amino-3-(methylsulfanyl)propan-1-ol has a branched structure with the amino and hydroxyl groups attached to the same carbon atom, along with the methylsulfanyl group attached to a neighboring carbon atom.

Upstream product

• 34017-27-1 S-methyl-L-cysteine methyl ester hydrochloride salt 
• 1187-84-4 S-methyl-L-cysteine 
• 125509-78-6 (R)-cysteinol 

Downstream Products

• 1420379-69-6 (R)-4-(methylthiomethyl)-2-(2-hydroxyphenyl)-2-oxazoline 
• 69977-58-8 ((R)-1-Hydroxymethyl-2-methylsulfanyl-ethyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis, opiate receptor binding and analgesic activity of enkephalin analogues

The synthesis and biological testing of analogues of Met-enkephalin, a recently discovered opioid peptide from mammalian brain, are described. Testing involved determination of affinity constants for an opiate receptor site and of analgesic potency in the tail-flick test in mouse. The effects on opioid activity on modifying various parts of the enkephalin molecule are discussed. Tyr-D-Ala-Gly-MePhe-Met(O)-ol1) (FK 33-824), which was highly active in these tests, was subsequently selected for clinical testing. The use of two complementary models - in vitro binding studies and in vivo test for analgesia - for the assessment of biological activity in the evaluation of analogues is explained.

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

Bifunctional bis(oxazolines) as potential ligands in catalytic asymmetric reactions

C2-symmetrical bis(oxazoline) ligands bearing pendant alkylthio ether groups were synthesized, and the structures of Cu complexes were determined by single crystal X-ray diffraction. The potential utility in catalysis was shown in the asymmetric addition of methyllithium to an aromatic aldimine, which resulted in a mixture of products with an enantiomeric excess of 68%.

First generation cysteine- and methionine-derived oxazolidine and thiazolidine ligands for palladium-catalyzed asymmetric allylations

A new series of enantiopure oxazolidine-thioether and thiazolidine-alcohol ligands have been synthesized from L-cysteine, S-methyl-L-cysteine, and L-methionine in a straightforward manner that allows numerous structural variations to be formed. These types of ligands have not previously been used in asymmetric palladium-catalyzed allylations and their efficacy was explored in the reaction of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate. The reaction proceeds in excellent yield and with good enantioselectivity. The palladium catalyst derived from N-benzyl-2,2-dimethyl-4-(2-thiapropyl) oxazolidine (12) provides the allylation product in a quantitative yield and with an enantiomeric excess of 94%. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Palladium-catalysed Asymmetric Allylic Substitution: a Ligand Design Incorporating Steric and Electronic Effects

Enantiomerically pure ligands containing a 4,5-dihydrooxazole moiety tethered to an auxiliary sulfur or phosphorus donor have been prepared.These ligands have been exploited for palladium-catalysed asymmetric allylic substitution, providing enantioselectivity in the catalytic reaction is discussed in terms of the steric and electronic influences provided by the ligand.

Aldehyde derivatives and their use as calpain inhibitors

Aldehyde derivatives with a specific calpain inhibiting activity and a platelet-aggregation inhibiting effect with formula (I) or formula (II): wherein R1 represents an aromatic hydrocarbon group, a heterocyclic group, or a group of-X-R3 in which X represents O,-S(O)m-(m = 0, 1, or 2), and R3 represents an aromatic hydrocarbon group, a heterocyclic group, or an alkyl group; Z represents R?-Y-or R?O-CH(R?)-in which Y represents a 3-to 7-membered nitrogen-containing saturated heterocyclic group, or a single cyclic saturated hydrocarbon group, R? represents an alkyl group, an alkenyl group, an alkynyl group, an acyl group, a sulfonyl group, an alkoxycarbonyl group, a carbamoyl group, or a thiocarbamoyl group, R? represents hydrogen, an alkyl group, or an aromatic hydrocarbon group, and R? represents an acyl group, a carbamoyl group, a thiocarbamoyl group, or an alkyl group; and n is an integer of 1 to 5. wherein R?, R?, R?, and R1? are defined in the specification.

Pyrimidinylpropenamides as antitumor agents. Analogues of the antibiotic sparsomycin

A series of pyrimidinylpropenamides 9 and their oxidation products 10 was prepared, as analogues of sparsomycin (1), for antitumor evaluation. Syntheses involved condensation of the appropriate amino alcohol 5 with acid 8. The resulting sulfides 9 were then oxidized with NaIO4 or H2O2 to sulfoxides 10. Activity was studied in lymphocytic leukemia P-388 and KB cell culture. With the exception of the n-decyl analogue, all of the deoxygenated compounds 9 were inactive regardless of the sterochemical form. In the sulfoxide series 10, those compounds prepared with an L configuration at the asymmetric carbon were also inactive. The completely racemic sulfoxides, on the other hand, displayed substantial antitumor activity (ILS=37-61% in P-388; ED50=1.2-2.4μg/ml in KB) suggesting that both the presence of a sulfoxide moiety and a D configuration at the chiral carbon atom were structural requirements for a positive antitumor response. There appeared to be a large tolerance for the group substituted at the sulfoxide moiety, however.