(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

Base Information

Chemical Name:(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid
CAS No.:914638-85-0
Molecular Formula:C₃₉H₄₄O₇
Molecular Weight:624.774
Hs Code.:

Synonyms:(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

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Chemical Property of (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

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Technology Process of (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

There total 20 articles about (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid 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:

: (E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enal

: 914638-85-0
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 0 - 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-92-9
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-en-1-ol

: 914638-85-0
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

Guidance literature:: Multi-step reaction with 15 steps

1.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

2.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

2.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

3.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

5.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

6.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

7.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

8.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: 80 percent / K-Selectride / tetrahydrofuran / 3 h / -78 °C

11.1: 95 percent / Red-Al / diethyl ether / 2 h / 0 - 20 °C

12.1: 75 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 - 20 °C

13.1: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

14.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

15.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetrachloromethane; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless epoxidation / 14.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.08.035

Reference yield:

: 914638-72-5
(E)-(S)-4-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-2-enoic acid ethyl ester

: 914638-85-0
(E)-(3S,4S,7S,9R)-3,4,7-Tris-benzyloxy-9-(4-methoxy-benzyloxy)-dec-5-enoic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: 65 percent / LiAlH₄; AlCl₃ / diethyl ether / 6 h / 0 °C

2.1: 85 percent / cumene hydroperoxide; (iPrO)4Ti / (+)-DIPT / CH₂Cl₂ / 12 h / -20 °C

3.1: CCl₄; Ph₃P; NaHCO₃ / 1 h / Heating

3.2: LDA / tetrahydrofuran / 3 h / -78 - -40 °C

4.1: 80 percent / NaH / tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 85 percent / CSA / methanol / 0.5 h / 20 °C

6.1: 75 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

7.1: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: 75 percent / NaH / tetrahydrofuran / 12 h / 0 - 20 °C

9.1: 70 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

10.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 80 percent / K-Selectride / tetrahydrofuran / 3 h / -78 °C

12.1: 95 percent / Red-Al / diethyl ether / 2 h / 0 - 20 °C

13.1: 75 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 - 20 °C

14.1: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

15.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

16.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetrachloromethane; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; 2-methyl-but-2-ene; oxalyl dichloride; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Sharpless epoxidation / 15.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.08.035