(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester
CAS No.:641613-74-3
Molecular Formula:C₃₀H₄₀O₉
Molecular Weight:544.642
Hs Code.:

Synonyms:(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

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Chemical Property of (E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

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Technology Process of (E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

There total 8 articles about (E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid 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: 61.0%

: 18295-66-4
1-ethoxy-1-(trimethylsiloxy)ethene

: 641613-73-2
Acetic acid (E)-(4R,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-7-oxo-hept-2-enyl ester

: (E)-(3S,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

: 641613-74-3
(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

Guidance literature:: With titanium(IV) dichlorodiisopropylate; In toluene; at -78 ℃;
DOI:10.1016/j.tetlet.2003.09.141

Reference yield:

: (2S,3R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-bis-(4-methoxy-benzyloxy)-pentanal

: 641613-74-3
(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 546 mg / CH₂Cl₂ / 4 h / Heating

2.1: DIBAL / diethyl ether / 12 h / -78 - 20 °C

3.1: 1.18 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: TBAF / tetrahydrofuran / 24 h / 20 °C

5.1: 3.76 g / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

6.1: TiCl₄; Ti(O-i-Pr)4 / toluene / 0.17 h / -78 °C

6.2: 61 percent / toluene / 2 h / -78 °C

With titanium(IV) isopropylate; dmap; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Wittig olefination / 6.2: Mukaiyama reaction;
DOI:10.1002/chem.200500892

Reference yield:

: 641613-77-6
Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

: 641613-74-3
(E)-(3R,5R,6R)-9-Acetoxy-3-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-8-methyl-non-7-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 3.76 g / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: TiCl₄; Ti(O-i-Pr)4 / toluene / 0.17 h / -78 °C

2.2: 61 percent / toluene / 2 h / -78 °C

With titanium(IV) isopropylate; titanium tetrachloride; Dess-Martin periodane; In dichloromethane; toluene; 2.2: Mukaiyama reaction;
DOI:10.1002/chem.200500892