(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester
CAS No.:438002-62-1
Molecular Formula:C₅₃H₆₈O₁₀SeSi
Molecular Weight:972.162
Hs Code.:

(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

Synonyms:(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

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Chemical Property of (E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

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Technology Process of (E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

There total 16 articles about (E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-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:

: 922-67-8
propynoic acid methyl ester

: 438002-94-9
(2R,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

: 438002-62-1
(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 45h;
DOI:10.1021/jo010974p

Reference yield:

: 131310-61-7
(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 438002-62-1
(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

2.1: p-toluenesulfonic acid hydrate / methanol; CH₂Cl₂ / 19.5 h / 20 °C

3.1: NaH / dimethylformamide / 0.25 h / 20 °C

3.2: 35.53 g / dimethylformamide / 16 h / 20 °C

4.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

5.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

6.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

7.1: NaH / dimethylformamide / 0.5 h / 20 °C

7.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

8.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

9.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

10.1: 2.60 g / scandium trifluoromethanesulfonate / benzene / 31.5 h / 20 °C

11.1: DIBALH / toluene; hexane / 30 h / 0 °C

11.2: 89 percent / toluene; hexane; CH₂Cl₂ / 3 h / 20 °C

12.1: TBAF / tetrahydrofuran / 11.5 h / 20 °C

13.1: 471.1 mg / imidazole / dimethylformamide / 2.5 h / 0 °C

14.1: 8.72 g / N-methylmorpholine / CH₂Cl₂ / 45 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; magnesium bromide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jo010974p

Reference yield:

: 100-39-0
benzyl bromide

: 438002-62-1
(E)-3-((2S,3R,5S,6R)-5-Benzyloxy-2-{(1R,3S)-1-benzyloxy-3-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-3-phenylselanyl-propyl}-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaH / dimethylformamide / 0.25 h / 20 °C

1.2: 35.53 g / dimethylformamide / 16 h / 20 °C

2.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

4.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 20 °C

5.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

6.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

7.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

8.1: 2.60 g / scandium trifluoromethanesulfonate / benzene / 31.5 h / 20 °C

9.1: DIBALH / toluene; hexane / 30 h / 0 °C

9.2: 89 percent / toluene; hexane; CH₂Cl₂ / 3 h / 20 °C

10.1: TBAF / tetrahydrofuran / 11.5 h / 20 °C

11.1: 471.1 mg / imidazole / dimethylformamide / 2.5 h / 0 °C

12.1: 8.72 g / N-methylmorpholine / CH₂Cl₂ / 45 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; magnesium bromide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jo010974p