(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

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Chemical Name:(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester
CAS No.:782472-60-0
Molecular Formula:C₄₃H₆₀O₉S
Molecular Weight:753.01
Hs Code.:

Synonyms:(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

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Chemical Property of (3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

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Technology Process of (3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

There total 15 articles about (3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl 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:

: 782472-50-8
(E)-(R)-5-(4-Methoxy-benzyloxy)-dec-2-enoic acid methyl ester

: 782472-60-0
(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 79 percent / DIBAL-H / CH₂Cl₂ / 3 h / 20 °C

2: 83 percent / cumene hydroperoxide; (-)-DIPT; Ti(Oi-Pr)4 / CH₂Cl₂ / 3 h / -20 °C

3: 80 percent / NaAlH₂(OCH₂CH₂OMe)2 / tetrahydrofuran / 5 h / 0 °C

4: 84 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

5: 78 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

6: 89 percent / TBAF / CH₂Cl₂ / 10 h / 20 °C

7: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

8: 83 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 10 h / 0 - 20 °C

9: 68 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 16 h / 20 °C

10: 73 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 0 - 20 °C

11: 66 percent / 2,4,6-trichlorobenzoyl cloride; Et₃N; DMAP / tetrahydrofuran; toluene / 20 h / 20 °C

12: 69 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium chlorite; oxalyl dichloride; Cumene hydroperoxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 2: Sharpless asymmetric epoxidation / 7: Swern oxidation;
DOI:10.1016/j.tetlet.2004.08.052

Reference yield:

: 782472-49-5
(R)-3-(4-Methoxy-benzyloxy)-octanal

: 782472-60-0
(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 85 percent / benzene / 2 h / Heating

2: 79 percent / DIBAL-H / CH₂Cl₂ / 3 h / 20 °C

3: 83 percent / cumene hydroperoxide; (-)-DIPT; Ti(Oi-Pr)4 / CH₂Cl₂ / 3 h / -20 °C

4: 80 percent / NaAlH₂(OCH₂CH₂OMe)2 / tetrahydrofuran / 5 h / 0 °C

5: 84 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

6: 78 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

7: 89 percent / TBAF / CH₂Cl₂ / 10 h / 20 °C

8: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

9: 83 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 10 h / 0 - 20 °C

10: 68 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 16 h / 20 °C

11: 73 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 0 - 20 °C

12: 66 percent / 2,4,6-trichlorobenzoyl cloride; Et₃N; DMAP / tetrahydrofuran; toluene / 20 h / 20 °C

13: 69 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium chlorite; oxalyl dichloride; Cumene hydroperoxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 3: Sharpless asymmetric epoxidation / 8: Swern oxidation;
DOI:10.1016/j.tetlet.2004.08.052

Reference yield:

: {(2S,3R)-3-[(R)-2-(4-Methoxy-benzyloxy)-heptyl]-oxiranyl}-methanol

: 782472-60-0
(3R,5R)-3-Benzyloxy-5-hydroxy-decanoic acid (R)-1-{(R)-2-benzyloxy-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-propyl}-hexyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / NaAlH₂(OCH₂CH₂OMe)2 / tetrahydrofuran / 5 h / 0 °C

2: 84 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

3: 78 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

4: 89 percent / TBAF / CH₂Cl₂ / 10 h / 20 °C

5: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

6: 83 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 10 h / 0 - 20 °C

7: 68 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; toluene / 16 h / 20 °C

8: 73 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 0 - 20 °C

9: 66 percent / 2,4,6-trichlorobenzoyl cloride; Et₃N; DMAP / tetrahydrofuran; toluene / 20 h / 20 °C

10: 69 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; dmap; sodium chlorite; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 5: Swern oxidation;
DOI:10.1016/j.tetlet.2004.08.052