(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Base Information

Chemical Name:(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester
CAS No.:867061-54-9
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

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Chemical Property of (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

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Technology Process of (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

There total 11 articles about (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic 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: 94.0%

: 867061-64-1
(E)-3-[(1S,3R)-3-Benzyloxy-1-(2-iodo-ethyl)-pentyloxy]-2-methyl-acrylic acid methyl ester

: 867061-54-9
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Guidance literature:: With air; triethyl borane; tris-(trimethylsilyl)silane; In hexane; toluene; at 20 ℃; for 1h;
DOI:10.1021/jo051107d

Reference yield:

: 256486-04-1
(R)-3-Benzyloxy-pentan-1-ol

: 867061-54-9
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 60 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 85 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: dimethyl sulfode / CH₂Cl₂ / 2 h / 20 °C

4.1: 126 mg / NaBH₄ / methanol / 1 h / 20 °C

5.1: 89.7 percent / Et₃N / CH₂Cl₂ / 8 h / 0 °C

6.1: 69.1 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

7.1: 78.4 percent / NaI / acetone / 3 h / Heating

8.1: 94 percent / TTMSS; Et₃B; air / toluene; hexane / 1 h / 20 °C

With sodium tetrahydroborate; air; pyridine-SO₃ complex; triethyl borane; tris-(trimethylsilyl)silane; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; dimethyl sulfoxide; triethylamine; sodium iodide; In methanol; hexane; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/jo051107d

Reference yield:

: 256486-03-0
(R)-3-Benzyloxy-pentanoic acid methyl ester

: 867061-54-9
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / LiAlH₄ / diethyl ether / 1 h

2.1: 60 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 85 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: dimethyl sulfode / CH₂Cl₂ / 2 h / 20 °C

5.1: 126 mg / NaBH₄ / methanol / 1 h / 20 °C

6.1: 89.7 percent / Et₃N / CH₂Cl₂ / 8 h / 0 °C

7.1: 69.1 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

8.1: 78.4 percent / NaI / acetone / 3 h / Heating

9.1: 94 percent / TTMSS; Et₃B; air / toluene; hexane / 1 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; air; pyridine-SO₃ complex; triethyl borane; tris-(trimethylsilyl)silane; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; dimethyl sulfoxide; triethylamine; sodium iodide; In methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/jo051107d