para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside

Base Information

• Chemical Name: para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside
• CAS No.: 1632132-64-9
• Molecular Formula: C₁₇H₁₇F₃O₅S
• Molecular Weight: 390.38
• Mol file: 1632132-64-9.mol

Synonyms:para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside

Chemical Property of para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside

There total 5 articles about para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside 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: 65.0%

4-trifluoromethylbenzenethiol (825-83-2) + D-glucal triacetate (2873-29-2) → para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632129-92-0) + para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632132-64-9)

Guidance literature:

With zinc trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1340552

Reference yield:

4-methylphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside → para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632129-92-0) + para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632132-64-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / dichloromethane / 1 h / 0 °C

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: pyridine; dmap / dichloromethane / 1 h / 20 °C

4.1: bis(benzonitrile)palladium(II) chloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / acetonitrile / 12 h / 90 °C / Inert atmosphere

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(benzonitrile)palladium(II) chloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.1c03302

Reference yield:

1,5-anhydro-4,6-di-O-acetyl-2-deoxy-D-ribo-hex-1-enitol → para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632129-92-0) + para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside (1632132-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / dichloromethane / 1 h / 0 °C

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: pyridine; dmap / dichloromethane / 1 h / 20 °C

3.1: bis(benzonitrile)palladium(II) chloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / acetonitrile / 12 h / 90 °C / Inert atmosphere

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(benzonitrile)palladium(II) chloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.1c03302

upstream raw materials:

4-trifluoromethylbenzenethiol

D-glucal triacetate

4,6-di-O-acetyl-3-O-D-glucal

D-glucose

Refernces

• 1、 Jiang, Xuefeng,Li, Jiagen,Wang, Ming. "Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement". . p. 9053 - 9057. Retrieved 2021/11/30.