(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Base Information

Chemical Name:(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester
CAS No.:867061-58-3
Molecular Formula:C₂₉H₄₄O₇
Molecular Weight:504.664
Hs Code.:

(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

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Chemical Property of (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

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Technology Process of (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

There total 14 articles about (S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl 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:

: C₂₅H₂₇Cl₃O₅

: 54594-23-9
methyl nonactate

: 867061-58-3
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: With dmap; In benzene; at 20 ℃; for 2h;
DOI:10.1021/jo051107d

Reference yield:

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

: 867061-58-3
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: Multi-step reaction with 11 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

9.1: 91 percent / LiOH*H₂O / methanol; H₂O / 5 h / 20 °C

10.1: Et₃N / tetrahydrofuran / 2 h / 20 °C

11.1: 41 mg / 4-dimethylaminopyridine / benzene / 2 h / 20 °C

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

Reference yield:

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

: 867061-58-3
(S)-2-[(2S,5R)-5-((R)-2-Benzyloxy-butyl)-tetrahydro-furan-2-yl]-propionic acid (R)-2-[(2R,5S)-5-((S)-1-methoxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: Multi-step reaction with 12 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

10.1: 91 percent / LiOH*H₂O / methanol; H₂O / 5 h / 20 °C

11.1: Et₃N / tetrahydrofuran / 2 h / 20 °C

12.1: 41 mg / 4-dimethylaminopyridine / benzene / 2 h / 20 °C

With dmap; lithium hydroxide; 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 tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/jo051107d