Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 553663-07-3
• Molecular Formula: C₂₇H₂₉IO₉S
• Molecular Weight: 656.492
• Mol file: 553663-07-3.mol

Synonyms:Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 5 articles about Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 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: 89.0%

acetic anhydride (108-24-7) + (4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carbothioic acid S-[2-(2-iodo-phenyl)-ethyl] ester (553663-06-2) → Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (553663-07-3)

Guidance literature:

With pyridine; dmap; for 3h;

DOI:10.1021/ol034741r

Reference yield:

methyl acetyl of methyl phenylglyoxylate (85810-81-7) → Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (553663-07-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 1 h / 0 °C

1.2: TMSOTf / CH₂Cl₂

2.1: AlMe₃ / hexane; toluene / 5 h / Heating

3.1: 450 mg / TBAF / CH₂Cl₂; hexane / 1 h / 20 °C

4.1: 89 percent / pyridine; DMAP / 3 h

With pyridine; dmap; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; In hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol034741r

Reference yield:

2-(2-iodophenyl)-1-ethanethiol (177748-62-8) → Acetic acid (4aR,6R,7R,8S,8aS)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (553663-07-3)

Guidance literature:

Multi-step reaction with 3 steps

1: AlMe₃ / hexane; toluene / 5 h / Heating

2: 450 mg / TBAF / CH₂Cl₂; hexane / 1 h / 20 °C

3: 89 percent / pyridine; DMAP / 3 h

With pyridine; dmap; tetrabutyl ammonium fluoride; trimethylaluminum; In hexane; dichloromethane; toluene;

DOI:10.1021/ol034741r

upstream raw materials:

acetic anhydride

(4aR,6R,7R,8R,8aR)-7,8-Dihydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carbothioic acid S-[2-(2-iodo-phenyl)-ethyl] ester

methyl acetyl of methyl phenylglyoxylate

2-(2-iodophenyl)-1-ethanethiol

Downstream raw materials:

methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-galactopyranoside