4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide

Base Information

• Chemical Name: 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide
• CAS No.: 201546-84-1
• Molecular Formula: C₁₂H₁₅NO₃S₃
• Molecular Weight: 317.454
• Mol file: 201546-84-1.mol

Synonyms:4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide

Chemical Property of 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide

There total 17 articles about 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide 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: 86.0%

4-cyanophenyl 1,5-dithio-β-D-arabinopyranoside (130782-54-6) → 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide (201546-84-1)

Guidance literature:

With hydrogen sulfide; In pyridine; triethylamine; Ambient temperature;

DOI:10.1016/S0008-6215(98)00088-3

Reference yield:

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide (201546-84-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) CuSO₄; 2.) HCl / 1.) H₂SO₄, 20 deg C, 24 h; 2.) MeOH, 40 deg C, 100 min

2: 61 percent / Et₃N, SOCl₂ / CH₂Cl₂ / 0.25 h / -30 °C

3: 19 percent / dimethylformamide / 5 h / 100 °C

4: 1.) NaOMe; 2.) 10percent aq. HCl / 1.) r.t., 1 h; 2.) MeOH, reflux, 1 h

5: pyridine / 24 h / Ambient temperature

6: 74 percent / conc. H₂SO₄ / 1 h / 0 °C

7: Me₃SiOTf / 1,2-dichloro-ethane / 1 h / Ambient temperature

8: 96 percent / NaOMe / methanol / 0.5 h / Ambient temperature

9: 86 percent / H₂S / pyridine; triethylamine / Ambient temperature

With hydrogenchloride; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen sulfide; sodium methylate; copper(II) sulfate; triethylamine; In pyridine; methanol; dichloromethane; 1,2-dichloro-ethane; triethylamine; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00088-3

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide (201546-84-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 61 percent / Et₃N, SOCl₂ / CH₂Cl₂ / 0.25 h / -30 °C

2: 19 percent / dimethylformamide / 5 h / 100 °C

3: 1.) NaOMe; 2.) 10percent aq. HCl / 1.) r.t., 1 h; 2.) MeOH, reflux, 1 h

4: pyridine / 24 h / Ambient temperature

5: 74 percent / conc. H₂SO₄ / 1 h / 0 °C

6: Me₃SiOTf / 1,2-dichloro-ethane / 1 h / Ambient temperature

7: 96 percent / NaOMe / methanol / 0.5 h / Ambient temperature

8: 86 percent / H₂S / pyridine; triethylamine / Ambient temperature

With hydrogenchloride; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen sulfide; sodium methylate; triethylamine; In pyridine; methanol; dichloromethane; 1,2-dichloro-ethane; triethylamine; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00088-3

upstream raw materials:

4-cyanophenyl 1,5-dithio-β-D-arabinopyranoside

D-Xylose

methyl 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranoside

1,2,3,4-tetra-O-acetyl-5-thio-α-D-xylopyranose

Downstream raw materials:

4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzimidic acid methyl ester; hydriodide