ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

Base Information

• Chemical Name: ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate
• CAS No.: 1185202-64-5
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 1185202-64-5.mol

Synonyms:ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

Chemical Property of ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

There total 8 articles about ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate 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: 86.0%

(4S,6S,7S,E)-ethy 10-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-4-hydroxy-6-methyldec-2-enoate (1262206-08-5) → ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate (1185202-64-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol102658d

Reference yield:

4-benzyloxybutanal (5470-84-8) → ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate (1185202-64-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: titanium tetrachloride / dichloromethane / 0.25 h / -15 °C / Inert atmosphere

1.2: 0.5 h / -15 °C / Inert atmosphere

1.3: 1 h / -15 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

4.1: benzene / Reflux; Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: 20 % Pd(OH)2/C; hydrogen; triethylamine / benzene / 0.17 h / 20 °C / Inert atmosphere

7.1: Nitrosobenzene; D-Prolin / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere

7.2: 0.5 h / 20 °C / Inert atmosphere

7.3: 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 20 % Pd(OH)2/C; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; Nitrosobenzene; D-Prolin; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 7.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol102658d

Reference yield:

C20H28O5 (1185202-63-4) → ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate (1185202-64-5)

Guidance literature:

C₂₀H₂₈O₅; With samarium diiodide; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h; Inert atmosphere;

With water; sodium hydrogencarbonate; sodium sulfite; In tetrahydrofuran; methanol; Inert atmosphere;

DOI:10.1021/ol9015755

upstream raw materials:

C₂₀H₂₈O₅

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-(terttertbutyldimethylsilyloxy)-2-methylhexan-1-one

(4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate

Refernces

• 1、 Fadeyi, Olugbeminiyi O.,Lindsley, Craig W.. "Total synthesis of brevisamide". supporting information; experimental part. p. 3950 - 3952. Retrieved 2009/12/05.