(1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane

Base Information

• Chemical Name: (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane
• CAS No.: 127258-12-2
• Molecular Formula: C₁₆H₂₁IO₅
• Molecular Weight: 420.244

Synonyms:(1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane

Chemical Property of (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane

Chemical Property:

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Technology Process of (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane

There total 2 articles about (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane 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: 87.0%

[(1S,3R,5R,6R,8S,9R)-8-Methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]non-6-yl]-methanol (127258-10-0) → (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane (127258-12-2)

Guidance literature:

With pyridine; iodine; triphenylphosphine; In benzene; at 45 ℃; for 44h;

DOI:10.1021/jo00296a040

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane (127258-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) camphorsulfonic acid , 2.) n-Bu₄NF / 1.) benzene, reflux , 1h, 2.) THF, 6h, RT

2: 87 percent / I₂, PPh₃, pyridine / benzene / 44 h / 45 °C

With pyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In benzene;

DOI:10.1021/jo00296a040

Reference yield:

(1S,3R,5R,6S,8S,9R)-6-Iodomethyl-8-methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]nonane (127258-12-2) → (2S,4S,5R,6R)-2-(4-methoxyphenyl)-5-methyl-6-vinyl-1,3-dioxane-4-carboxaldehyde (127308-74-1)

Guidance literature:

With pyridine; zinc; In ethanol; for 0.166667h; Heating;

DOI:10.1021/jo00296a040

upstream raw materials:

[(1S,3R,5R,6R,8S,9R)-8-Methoxy-3-(4-methoxy-phenyl)-9-methyl-2,4,7-trioxa-bicyclo[3.3.1]non-6-yl]-methanol

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(2S,4S,5R,6R)-2-(4-methoxyphenyl)-5-methyl-6-vinyl-1,3-dioxane-4-carboxaldehyde

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