(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester
CAS No.:169895-52-7
Molecular Formula:C₃₀H₃₈O₇
Molecular Weight:510.628
Hs Code.:

Synonyms:(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

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Chemical Property of (E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

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Technology Process of (E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

There total 14 articles about (E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-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: 81.0%

: 169895-51-6
(E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

: 169895-52-7
(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; for 13h; Ambient temperature;
DOI:10.1021/jo9807619

Reference yield: 79.0%

: (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

: 169895-52-7
(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; Ambient temperature;
DOI:10.1016/00404-0399(50)10972-

Reference yield:

: 100-39-0
benzyl bromide

: 169895-52-7
(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 98 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / HCl / methanol / 5 h / Ambient temperature

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1.5 h, 2.) DMF, rt, 12 h

4: 99 percent / imidazole / dimethylformamide / 2 h / 0 °C

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to rt

6: 91 percent / benzene / 1 h / Heating

7: 87 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8: (+)-DET, Ti(i-PrO)4, t-BuO₂H, 4 Angstroem MS / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

9: SO₃*py, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / Ambient temperature

10: benzene / 11 h / Ambient temperature

11: 100 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

12: 81 percent / CSA / CH₂Cl₂ / 13 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9807619