(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl ester
CAS No.:908866-12-6
Molecular Formula:C₂₈H₃₄O₇
Molecular Weight:482.574
Hs Code.:

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

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

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

There total 10 articles about (E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl 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:

: 924656-64-4
(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(2-[1,3]dithian-2-yl-ethyl)-oxepan-3-yloxy]-acrylic acid methyl ester

: 908866-12-6
(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl ester

Guidance literature:: With water; sodium hydrogencarbonate; methyl iodide; In acetonitrile; at 35 ℃;
DOI:10.1021/ja062524q

Reference yield:

: 850656-74-5
((2R,4aR,6S,7R,9aS)-7-Benzyloxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

: 908866-12-6
(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

4.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

5.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

5.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

6.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

7.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

8.1: 1.57 g / 4-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

9.1: 1.27 g / NaHCO₃; MeI / acetonitrile; H₂O / 35 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; osmium(VIII) oxide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; copper(I) bromide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 8.1: Michael reaction;
DOI:10.1021/ja066772y

Reference yield:

: (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

: 908866-12-6
(E)-3-[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-(3-oxo-propyl)-oxepan-3-yloxy]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

4.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

5.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

6.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

7.1: 1.57 g / 4-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

8.1: 1.27 g / NaHCO₃; MeI / acetonitrile; H₂O / 35 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; osmium(VIII) oxide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; copper(I) bromide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; acetonitrile; tert-butyl alcohol; 7.1: Michael reaction;
DOI:10.1021/ja066772y