((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

Base Information

• Chemical Name: ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester
• CAS No.: 212205-70-4
• Molecular Formula: C₃₃H₅₁BrO₇
• Molecular Weight: 639.668
• Mol file: 212205-70-4.mol

Synonyms:

Chemical Property of ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

There total 7 articles about ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-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:

1,2-epoxytetradecane (3234-28-4) → ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (212205-70-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / <(S,S)-bis(2-hydroxy-3,5-bis(tert-butyl)benzylidene)cyclohexane-1,2-diamine>cobalt(III) acetate, H₂O / various solvent(s) / 0 - 20 °C

2: 1.) CSA, 2.) DIBALH / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -78 deg C

3: TEMPO, NaOCl, NaBr, NaHCO₃ / toluene; ethyl acetate; H₂O / 0 °C

4: MgBr₂*OEt₂ / CH₂Cl₂ / -78 °C

5: 92 percent / NaH / tetrahydrofuran / 0 - 20 °C

6: EDC, DMAP / CH₂Cl₂ / 0 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; camphor-10-sulfonic acid; water; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium bromide; magnesium bromide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo9810765

Reference yield:

(R)-tetradecane-1,2-diol (153062-86-3) → ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (212205-70-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) CSA, 2.) DIBALH / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -78 deg C

2: TEMPO, NaOCl, NaBr, NaHCO₃ / toluene; ethyl acetate; H₂O / 0 °C

3: MgBr₂*OEt₂ / CH₂Cl₂ / -78 °C

4: 92 percent / NaH / tetrahydrofuran / 0 - 20 °C

5: EDC, DMAP / CH₂Cl₂ / 0 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium bromide; magnesium bromide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo9810765

Reference yield:

(R)-2-Methoxymethoxy-tetradecanal (114379-36-1) → ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester (212205-70-4)

Guidance literature:

Multi-step reaction with 3 steps

1: MgBr₂*OEt₂ / CH₂Cl₂ / -78 °C

2: 92 percent / NaH / tetrahydrofuran / 0 - 20 °C

3: EDC, DMAP / CH₂Cl₂ / 0 °C

With dmap; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; magnesium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo9810765

upstream raw materials:

1,2-epoxytetradecane

(R)-tetradecane-1,2-diol

(R)-2-Methoxymethoxy-tetradecanal

2-((4-bromobenzyl)oxy)acetaldehyde

Downstream raw materials:

(S)-[(2R,6S)-6-(4-Bromo-benzyloxymethyl)-5,6-dihydro-2H-pyran-2-yl]-((1R,2R)-2-methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid methyl ester