(R)-4-Isopropylthiazolidine-2-thione

Base Information

• Chemical Name: (R)-4-Isopropylthiazolidine-2-thione
• CAS No.: 110199-16-1
• Molecular Formula: C6H11 N S2
• Molecular Weight: 161.292
• Hs Code.: 2934999090
• European Community (EC) Number: 640-898-7
• DSSTox Substance ID: DTXSID70552526
• Wikidata: Q72486338
• Mol file: 110199-16-1.mol

Synonyms:(R)-4-Isopropylthiazolidine-2-thione;110199-16-1;(R)-4-isopropyl-1,3-thiazolidine-2-thione;(4R)-4-propan-2-yl-1,3-thiazolidine-2-thione;(R)-(+)-4-Isopropyl-1,3-thiazolidine-2-thione;(4R)-4-(propan-2-yl)-1,3-thiazolidine-2-thione;(4R)-4-Isopropyl-1,3-thiazolidine-2-thione;SCHEMBL9096955;DTXSID70552526;MFCD06658213;AKOS015920389;AKOS015995027;AC-30986;DS-14201;CS-0097413;A894923;J-502233;(R)-4-Isopropylthiazolidine-2-thione, >=98.0% (GC)

Chemical Property of (R)-4-Isopropylthiazolidine-2-thione

Chemical Property:

• Vapor Pressure: 0.0968mmHg at 25°C
• Melting Point: 69-71oC
• Boiling Point: 223.3oC at 760 mmHg
• PKA: 12.95±0.40(Predicted)
• Flash Point: 88.9°C
• PSA: 69.42000
• Density: 1.17g/cm³
• LogP: 1.96110
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 161.03329170
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

(R)-4-Isopropylthiazolidine-2-thione ≥98.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1CSC(=S)N1
• Isomeric SMILES: CC(C)[C@@H]1CSC(=S)N1
• Uses: Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

Technology Process of (R)-4-Isopropylthiazolidine-2-thione

There total 6 articles about (R)-4-Isopropylthiazolidine-2-thione 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: 87.0%

(3S,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-1-[(4'R)-4'-isopropyl-2'-thioxothiazolidin-3'-yl]-5-(4-methoxybenzyloxy)-hexan-1-one (950513-93-6) + ethanol (64-17-5) → ethyl (3S,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)hexanoate + 4(R)-isopropyl-1,3-thiazolidine-2-thione (110199-16-1)

Guidance literature:

With dmap; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2007.05.093

Reference yield: 77.0%

carbon disulfide (75-15-0,12122-00-8) + (R)-2-amino-3-methylbutanol (4276-09-9,473-75-6) → 4(R)-isopropyl-1,3-thiazolidine-2-thione (110199-16-1)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 72h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201601172 DOI:10.1002/ejoc.201501592

Reference yield:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) → 4(R)-isopropyl-1,3-thiazolidine-2-thione (110199-16-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 °C / Inert atmosphere; Reflux

2.1: potassium hydroxide / water / 4 h / Inert atmosphere

3.1: potassium hydroxide / water; ethanol / 72 h / Inert atmosphere; Reflux

With sodium tetrahydroborate; potassium hydroxide; In tetrahydrofuran; ethanol; water;

DOI:10.1021/jacs.5b05296

upstream raw materials:

(3R,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-1-[(4'R)-4'-isopropyl-2'-thioxothiazolidin-3'-yl]-5-(4-methoxybenzyloxy)-hexan-1-one

ethanol

(3S,5S)-6-(tert-butyldiphenylsiloxy)-3-hydroxy-1-[(4'R)-4'-isopropyl-2'-thioxothiazolidin-3'-yl]-5-(4-methoxybenzyloxy)-hexan-1-one

D-Val-OH

Downstream raw materials:

3-((benzyloxy)acetyl)-4(R)-isopropyl-1,3-thiazolidine-2-thione

4-Benzyloxy-1-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-butan-1-one

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione

(R)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)propan-1-one

Refernces

• 1、 Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong. "Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations". . p. 74 - 84. Retrieved 2017/12/26.
• 2、 McNulty, James,McLeod, David,Jenkins, Hilary A.. "Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment". . p. 688 - 692. Retrieved 2017/01/18.