(E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

Base Information

• Chemical Name: (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester
• CAS No.: 503026-44-6
• Molecular Formula: C₄₁H₅₀O₁₃S
• Molecular Weight: 782.906

Synonyms:(E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

Chemical Property of (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

There total 9 articles about (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-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: 77.0%

(E)-(4R,5S)-4-(4-Methoxy-benzyloxy)-5-{(E)-(4R,5S)-4-(4-methoxy-benzyloxy)-5-[(S)-3-(2-methoxy-ethoxymethoxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester (503026-43-5) → (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester (503026-44-6)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at -20 ℃; for 6h;

DOI:10.1016/S0040-4039(02)02284-0

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester (503026-44-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / tetrahydrofuran / 4 h / 0 - 20 °C

2: 75 percent / AcOH; water; HCl / 14 h / 20 °C

3: NaIO₄ / methanol; H₂O / 2 h / 20 °C

4: 1 h / 110 °C

5: 80 percent / HCl / dioxane; H₂O / 12 h / 20 °C

6: 84 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

7: 81 percent / DBN / benzene / 8 h / 20 °C

8: 82 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

9: 77 percent / TMSCl; NaI / acetonitrile / 6 h / -20 °C

With hydrogenchloride; dmap; sodium periodate; chloro-trimethyl-silane; 2,6-dichloro-benzonitrile; 2,4,6-trichlorobenzoyl chloride; water; acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(02)02284-0

Reference yield:

5-deoxy-3-O-(4-methoxybenzyl)-α,β-L-arabinofuranose → (E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester (503026-44-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaIO₄ / methanol; H₂O / 2 h / 20 °C

2: 1 h / 110 °C

3: 80 percent / HCl / dioxane; H₂O / 12 h / 20 °C

4: 84 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

5: 81 percent / DBN / benzene / 8 h / 20 °C

6: 82 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

7: 77 percent / TMSCl; NaI / acetonitrile / 6 h / -20 °C

With hydrogenchloride; dmap; sodium periodate; chloro-trimethyl-silane; 2,6-dichloro-benzonitrile; 2,4,6-trichlorobenzoyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(02)02284-0

upstream raw materials:

(E)-(4R,5S)-4-(4-Methoxy-benzyloxy)-5-{(E)-(4R,5S)-4-(4-methoxy-benzyloxy)-5-[(S)-3-(2-methoxy-ethoxymethoxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

p-Methoxybenzyl bromide

6-(4-methoxybenzyloxy)-2,2,5-trimethyl-(3aR,5S,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole

(E)-(4R,5S)-4-(4-Methoxy-benzyloxy)-5-[(S)-3-(2-methoxy-ethoxymethoxy)-butyryloxy]-hex-2-enoic acid

Downstream raw materials:

(7E,13E)-(4S,9R,10S,15R,16S)-9,15-Bis-(4-methoxy-benzyloxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

(+)-macrosphelide A

(E)-(4R,5S)-5-[(E)-(4R,5S)-5-((S)-3-Hydroxy-butyryloxy)-4-(4-methoxy-benzyloxy)-hex-2-enoyloxy]-4-(4-methoxy-benzyloxy)-hex-2-enoic acid

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