3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester
• CAS No.: 651322-83-7
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.418
• Mol file: 651322-83-7.mol

Synonyms:3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester

Chemical Property of 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester

There total 5 articles about 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl 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: 96.0%

3-(2-benzyloxymethyl-3,6-dimethoxy-phenyl)-3-hydroxy-propionic acid tert-butyl ester (651322-82-6) → 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester (651322-83-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃;

DOI:10.1002/anie.200352591

Reference yield:

acetic acid tert-butyl ester (540-88-5) → 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester (651322-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LDA / tetrahydrofuran / -78 °C

2: 96 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0 °C

With ammonium cerium(IV) nitrate; lithium diisopropyl amide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1002/anie.200352591

Reference yield:

2-(2-hydroxymethyl-3,6-dimethoxyphenyl)-1,3-dithiolane (151417-98-0) → 3-(2-benzyloxymethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-hydroxy-propionic acid tert-butyl ester (651322-83-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / NaH; tetrabutylammnoium iodide / tetrahydrofuran

2: 86 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H₂O

3: 99 percent / LDA / tetrahydrofuran / -78 °C

4: 96 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0 °C

With ammonium cerium(IV) nitrate; tetra-(n-butyl)ammonium iodide; sodium hydride; bis-[(trifluoroacetoxy)iodo]benzene; lithium diisopropyl amide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1002/anie.200352591

upstream raw materials:

3-(2-benzyloxymethyl-3,6-dimethoxy-phenyl)-3-hydroxy-propionic acid tert-butyl ester

acetic acid tert-butyl ester

2-(2-hydroxymethyl-3,6-dimethoxyphenyl)-1,3-dithiolane

2-benzyloxymethyl-3,6-dimethoxy-benzaldehyde

Downstream raw materials:

3-(8-benzyloxymethyl-11-hydroxy-2-methyl-4-octyloxymethoxy-3,7,10-trioxo-2,3,7,10-tetrahydro-1H-naphtho[2,3-e]isoindol-9-yl)-3-hydroxy-propionic acid tert-butyl ester