(1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester
• CAS No.: 367954-22-1
• Molecular Formula: C₁₉H₂₆O₅Si
• Molecular Weight: 362.498
• Mol file: 367954-22-1.mol

Synonyms:(1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester

Chemical Property of (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester

There total 4 articles about (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl 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: 90.0%

benzyl iodomethyl ether (17482-09-6) + methyl (1S,6R)-1-hydroxy-6-((trimethylsilyl)oxy)cyclohexa-2,4-diene-1-carboxylate (367954-21-0) → (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester (367954-22-1)

Guidance literature:

methyl (1S,6R)-1-hydroxy-6-((trimethylsilyl)oxy)cyclohexa-2,4-diene-1-carboxylate; With sodium hydride; In tetrahydrofuran; at -65 ℃;

benzyl iodomethyl ether; Further stages.;

DOI:10.1021/ol010151m

Reference yield:

sodium benzoate (532-32-1) → (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester (367954-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Alcaligenes eutrophus B₉ / various solvent(s) / 30 °C

2: cesium carbonate

3: 90 percent / NaH / tetrahydrofuran / -65 °C

With Alcaligenes eutrophus B₉; sodium hydride; caesium carbonate; In tetrahydrofuran;

DOI:10.1021/ol010151m

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → (1S,6R)-1-Benzyloxymethoxy-6-trimethylsilanyloxy-cyclohexa-2,4-dienecarboxylic acid methyl ester (367954-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: cesium carbonate

2: 90 percent / NaH / tetrahydrofuran / -65 °C

With sodium hydride; caesium carbonate; In tetrahydrofuran;

DOI:10.1021/ol010151m

upstream raw materials:

benzyl iodomethyl ether

methyl (1S,6R)-1-hydroxy-6-((trimethylsilyl)oxy)cyclohexa-2,4-diene-1-carboxylate

sodium benzoate

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

Downstream raw materials:

(1S,6R)-1-Benzyloxymethoxy-6-hydroxy-cyclohexa-2,4-dienecarboxylic acid methyl ester

Refernces