(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester
CAS No.:494760-58-6
Molecular Formula:C₃₇H₅₀O₇S₂
Molecular Weight:670.932
Hs Code.:

(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

Synonyms:(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

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Chemical Property of (E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

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Technology Process of (E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

There total 4 articles about (E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-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:

: 378742-02-0
[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane

: 494760-58-6
(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 1 h / 0 °C

1.2: 95 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 0 °C

2.1: aq. KBr; TEMPO; NaClO / NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

3.1: BF₃*OEt₃ / CH₂Cl₂ / -78 - 0 °C

4.1: 2.58 g / TBAF / tetrahydrofuran / 10 h / Heating

5.1: 94 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

With 4-methyl-morpholine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; dimethylsulfide borane complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium bromide; cyclohexene; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja036984k

Reference yield:

: 494760-56-4
2-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-ethanol

: 494760-58-6
(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: aq. KBr; TEMPO; NaClO / NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

2: BF₃*OEt₃ / CH₂Cl₂ / -78 - 0 °C

3: 2.58 g / TBAF / tetrahydrofuran / 10 h / Heating

4: 94 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

With 4-methyl-morpholine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja036984k

Reference yield:

: 494760-55-3
[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetaldehyde

: 494760-58-6
(E)-3-[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-[1,3]dithian-2-ylmethyl-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: BF₃*OEt₃ / CH₂Cl₂ / -78 - 0 °C

2: 2.58 g / TBAF / tetrahydrofuran / 10 h / Heating

3: 94 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

With 4-methyl-morpholine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja036984k