(S)-Methyl 3-(thiophen-2-ylthio)butanoate

Base Information

• Chemical Name: (S)-Methyl 3-(thiophen-2-ylthio)butanoate
• CAS No.: 133359-79-2
• Molecular Formula: C9H12O2S2
• Molecular Weight: 216.325
• DSSTox Substance ID: DTXSID40440365
• Nikkaji Number: J2.784.079E
• Mol file: 133359-79-2.mol

Synonyms:133359-79-2;(S)-Methyl 3-(thiophen-2-ylthio)butanoate;methyl (S)-3-(thiophen-2-ylthio)butanoate;(S)-Methyl3-(thiophen-2-ylthio)butanoate;DTXSID40440365;HWLDYKJDDGJZSN-ZETCQYMHSA-N;Methyl (S)-3-(2-Thienylthio)butyrate;(S)-3-(2-Thienylthio)butanoic acid methyl ester;METHYL (3S)-3-(THIOPHEN-2-YLSULFANYL)BUTANOATE

Chemical Property of (S)-Methyl 3-(thiophen-2-ylthio)butanoate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 216.02787197
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC(=O)OC)SC1=CC=CS1
• Isomeric SMILES: C[C@@H](CC(=O)OC)SC1=CC=CS1

Technology Process of (S)-Methyl 3-(thiophen-2-ylthio)butanoate

There total 1 articles about (S)-Methyl 3-(thiophen-2-ylthio)butanoate 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:

lithium 2-thienylmercaptide (96010-14-9) + methyl (R)-3-(p-toluenesulfonyloxy)butyrate (91366-12-0) → 2-thienyl disulfide (6911-51-9) + methyl (S)-3-(thiophen-2-ylthio)butyrate (133359-79-2) + methyl (S)-3-<<5-(2-thienylthio)-2-thienyl>thio>butyrate

Guidance literature:

In tetrahydrofuran; hexane; formamide; at 25 ℃; for 72h;

DOI:10.1021/jo00059a013

Reference yield: 78.9%

methyl (S)-3-(thiophen-2-ylthio)butyrate (133359-79-2) → (S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one (147086-79-1)

Guidance literature:

With trifluorormethanesulfonic acid; at 100 ℃; for 3.5h; Reagent/catalyst; Temperature;

Reference yield:

methyl (S)-3-(thiophen-2-ylthio)butyrate (133359-79-2) → dorzolamide (120279-96-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 45 g / 12 N HCl / H₂O / 3 h / Heating

2: trifluoroacetic anhydride / toluene / 1 h / 25 °C

3: LiAlH₄ / tetrahydrofuran; toluene / 0 - 5 °C

4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H₂O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h

5: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C

6: 89.6 percent / H₂SO₄ / 20 - 25 °C

7: chlorosulfonic acid / 12 h / 50 °C

8: conc. NH₄OH / tetrahydrofuran / 1 h / 0 - 5 °C

9: 1) borane-dimethyl sulfide, 2) H₂SO₄ / 1) THF, r.t.

With pyridine; hydrogenchloride; chlorosulfonic acid; ammonium hydroxide; sodium tungstate; lithium aluminium tetrahydride; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; trifluoroacetic anhydride; In tetrahydrofuran; water; ethyl acetate; toluene;

DOI:10.1021/jo00059a013

upstream raw materials:

lithium 2-thienylmercaptide

methyl (R)-3-(p-toluenesulfonyloxy)butyrate

Downstream raw materials:

(S)-3-(thien-2-ylthio)butyric acid

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran

5,6-dihydro-(R,S)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide

Refernces