(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

Base Information

• Chemical Name: (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
• CAS No.: 553663-06-2
• Molecular Formula: C₂₃H₂₅IO₇S
• Molecular Weight: 572.418
• Mol file: 553663-06-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

(4aR,6R,7R,8S,8aS)-6-Methoxy-2-phenyl-7,8-bis-trimethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carbothioic acid S-[2-(2-iodo-phenyl)-ethyl] ester → (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)

Guidance literature:

With tetrabutyl ammonium fluoride; In hexane; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol034741r

Reference yield:

methyl acetyl of methyl phenylglyoxylate (85810-81-7) → (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)

Guidance literature:

Multi-step reaction with 3 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

With 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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/ol034741r

upstream raw materials:

methyl acetyl of methyl phenylglyoxylate

2-(2-iodophenyl)-1-ethanethiol

(4aR,6R,7R,8S,8aS)-6-Methoxy-2-phenyl-7,8-bis-trimethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Downstream raw materials:

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

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

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