(1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol

Base Information

• Chemical Name: (1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol
• CAS No.: 16854-32-3
• Molecular Formula: C10H15 N O2 S
• Molecular Weight: 213.301
• Hs Code.: 2930909090
• European Community (EC) Number: 240-878-4
• Nikkaji Number: J236.872B
• Mol file: 16854-32-3.mol

Synonyms:16854-32-3;(1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol;(1S,2S)-(+)-Thiomicamine;(+)-Thiomicamine;(1S,2S)-2-Amino-1-(4-(methylthio)phenyl)propane-1,3-diol;(1S,2S)-2-amino-1-(4-methylsulfanylphenyl)propane-1,3-diol;[S(R*,R*)]-2-Amino-1-[p-(methylthio)phenyl]propane-1,3-diol;(S(R*,R*))-2-Amino-1-(p-(methylthio)phenyl)propane-1,3-diol;EINECS 240-878-4;SCHEMBL3252828;(1S,2S)-2-Amino-1-[4-(Methylsulfanyl)Phenyl]Propane-1,3-Diol;1,3-Propanediol, 2-amino-1-[4-(methylthio)phenyl]-, (1S,2S)-;MFCD00134212;AKOS015888927;(1S,2S)-(+)-Thiomicamine, 99%;AS-71094;BP-12579;CS-0059240;D73180;W-110444;1,3-Propanediol,2-amino-1-[4-(methylthio)phenyl]-,(1S,2S)-;(1S*,2S*)-(+)-2-Amino-1-[4-(methylsulfanyl)phenyl]-1,3-propanediol;1,3-Propanediol, 2-amino-1-(4-(methylthio)phenyl)-, (S-(R*,R*))-

Chemical Property of (1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol

Chemical Property:

• Vapor Pressure: 4.29E-08mmHg at 25°C
• Melting Point: 151-154 °C(lit.)
• Boiling Point: 428.2°Cat760mmHg
• PKA: 11.75±0.45(Predicted)
• Flash Point: 212.8°C
• PSA: 91.78000
• Density: 1.25g/cm³
• LogP: 1.46180
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 213.08234989
• Heavy Atom Count: 14
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

(1S,2S)-(+)-Thiomicamine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=CC=C(C=C1)C(C(CO)N)O
• Isomeric SMILES: CSC1=CC=C(C=C1)[C@@H]([C@H](CO)N)O
• Uses: (1S,2S)-(+)-Thiomicamine can be used:As a starting material in the synthesis of 3,4-dihydroisoquinolinium salts, which are employed as promoters in asymmetric epoxidation and oxidation?reactions.As a starting material in the synthesis of an α-amino acid named (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which is used to prepare modified peptides of biological importance.As a chiral base in the resolution of an angiotensin II type 2 receptor [AT2R] antagonist named EMA401.

Technology Process of (1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol

There total 14 articles about (1S,2S)-(+)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (23150-33-6,23150-34-7,27348-35-2,27348-43-2,27348-46-5,60658-37-9) → (1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (14172-52-2,16854-32-3,23150-35-8,27348-36-3,27348-47-6,27348-48-7,36624-58-5)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01141a074

Reference yield:

N-[1-hydroxymethyl-2-(4-methylsulfanyl-phenyl)-2-oxo-ethyl]-acetamide (38423-42-6) → (1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (14172-52-2,16854-32-3,23150-35-8,27348-36-3,27348-47-6,27348-48-7,36624-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminium isopropylate; isopropyl alcohol

2: aqueous HCl

With hydrogenchloride; aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01141a074

Reference yield:

(2RS,3SR)-2-amino-3-hydroxy-3-(4-methylsulfanyl-phenyl)-propionic acid ethyl ester (135266-97-6) → (1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (14172-52-2,16854-32-3,23150-35-8,27348-36-3,27348-47-6,27348-48-7,36624-58-5)

Guidance literature:

With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether;

upstream raw materials:

(1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

D-threo-1-p-methylmercaptophenyl-2-dichloroacetamidopropane-1,3-diol

(+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone

(1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

Downstream raw materials:

(1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

(R*,R*)-(+)-thiomicamine

(1S,2S)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

(R)-(4-Methylsulfanyl-phenyl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol

Refernces

• 1、 Giordano, Claudio,Cavicchioli, Silvia,Levi, Silvio,Villa, Marco. "NEW STRATEGY FOR RACEMIZATION OF 2-AMINO-1,3-PROPANEDIOLS, KEY INTERMEDIATES FOR THE SYNTHESIS OF ANTIBIOTIC DRUGS". . p. 5561 - 5564. Retrieved 2007/10/02.