(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester
CAS No.:370884-60-9
Molecular Formula:C₃₂H₄₂O₉
Molecular Weight:570.68
Hs Code.:

Synonyms:(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

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Chemical Property of (E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

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Technology Process of (E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

There total 23 articles about (E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic 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: 100.0%

: 623-47-2
propynoic acid ethyl ester

: 370884-58-5
1-[(2R,3S,6R,7S)-3-Hydroxy-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-propan-2-one

: 370884-60-9
(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

: 250226-93-8
(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

: 370884-60-9
(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

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

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

6.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

8.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

10.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

10.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

11.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

12.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

13.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

14.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

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

15.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

16.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

16.2: 91 percent / tetrahydrofuran / 1 h

17.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

17.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

18.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

18.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

19.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

20.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

20.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

21.1: 810 mg / TBAF / tetrahydrofuran / 16 h / 20 °C

22.1: 100 percent / 4-methylmorpholine / CH₂Cl₂ / 16 h / 30 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization / 15.1: Swern oxidation / 16.2: Wittig reaction / 18.1: Swern oxidation / 20.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 116237-17-3
4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

: 370884-60-9
(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 21 steps

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

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

5.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

7.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

9.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

10.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

11.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

12.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

13.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

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

14.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

15.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

15.2: 91 percent / tetrahydrofuran / 1 h

16.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

16.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

17.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

17.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

18.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

19.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

19.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

20.1: 810 mg / TBAF / tetrahydrofuran / 16 h / 20 °C

21.1: 100 percent / 4-methylmorpholine / CH₂Cl₂ / 16 h / 30 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; cyclohexene; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization / 14.1: Swern oxidation / 15.2: Wittig reaction / 17.1: Swern oxidation / 19.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X