ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate

Base Information

• Chemical Name: ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate
• CAS No.: 1333225-87-8
• Molecular Formula: C₁₉H₂₈O₅
• Molecular Weight: 336.428

Synonyms:ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate

Chemical Property of ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate

Chemical Property:

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Technology Process of ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate

There total 5 articles about ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-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:

(2E,5R,6S,7S,8S)-ethyl 8-benzyloxy-5,7-dihydroxy-6-methyl-2-nonenoate (1333225-81-2) → ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-87-8) + ethyl 2-[(2R,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-85-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 100 ℃; for 5.083h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol202210k

Reference yield:

(2S,4S,5R)-2-benzyloxy-5-hydroxy-4-methyl-7-octen-3-one (1333225-84-5) → ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-87-8) + ethyl 2-[(2R,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -35 - 0 °C / Inert atmosphere

2: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / 20 °C / Inert atmosphere

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 5.08 h / 100 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetramethylammonium triacetoxyborohydride; In dichloromethane; toluene; acetonitrile; 3: oxa-Michael cyclization;

DOI:10.1021/ol202210k

Reference yield:

(S)-2-benzyloxy-3-pentanone (132489-33-9) → ethyl 2-[(2S,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-87-8) + ethyl 2-[(2R,4R,5S,6S)-6-((S)-1-(benzyloxy)ethyl)-tetrahydro-4-hydroxy-5-methyl-2H-pyran-2-yl]acetate (1333225-85-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -35 - 0 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 5.08 h / 100 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; titanium tetrachloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; toluene; acetonitrile; 4.1: oxa-Michael cyclization;

DOI:10.1021/ol202210k

upstream raw materials:

(2S,4S,5R)-2-benzyloxy-5-hydroxy-4-methyl-7-octen-3-one

(2E,5R,6S,7S,8S)-ethyl 8-benzyloxy-5,7-dihydroxy-6-methyl-2-nonenoate

(2S,3S,4S,5R)-2-benzyloxy-4-methyl-7-octen-3,5-diol

(S)-2-benzyloxy-3-pentanone

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