4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide

Base Information

• Chemical Name: 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide
• CAS No.: 214272-33-0
• Molecular Formula: C₁₃H₁₇NO₃S₃*HI
• Molecular Weight: 459.393
• Mol file: 214272-33-0.mol

Synonyms:

Chemical Property of 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide

There total 17 articles about 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide 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: 82.0%

4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzamide (201546-84-1) + methyl iodide (74-88-4) → 4-((2S,3R,4S,5S)-3,4,5-Trihydroxy-tetrahydro-thiopyran-2-ylsulfanyl)-thiobenzimidic acid methyl ester; hydriodide (214272-33-0)

Guidance literature:

In acetone; for 2h; Heating;

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)-thiobenzimidic acid methyl ester; hydriodide (214272-33-0)

Guidance literature:

Multi-step reaction with 10 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

10: 82 percent / acetone / 2 h / Heating

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; acetone;

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)-thiobenzimidic acid methyl ester; hydriodide (214272-33-0)

Guidance literature:

Multi-step reaction with 9 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

9: 82 percent / acetone / 2 h / Heating

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; acetone;

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

upstream raw materials:

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

methyl iodide

D-Xylose

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