(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

Base Information

Chemical Name:(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane
CAS No.:385809-15-4
Molecular Formula:C₃₇H₅₈O₈SSi
Molecular Weight:691.014
Hs Code.:

(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

Synonyms:(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

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Chemical Property of (2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

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Technology Process of (2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

There total 37 articles about (2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane 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: 94.0%

: 107-30-2
chloromethyl methyl ether

: 385809-14-3
(2S,4RS,6R)-4-benzenesulfonyl-7-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-1-(4-methoxybenzyloxy)-6-methylheptan-2-ol

: 385809-15-4
(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 24h;
DOI:10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R

Reference yield:

: 527742-73-0
(6S)-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-2H-pyran-2-one

: 385809-15-4
(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 13 steps

1.1: CuI / 0 °C

1.2: 84 percent / diethyl ether / 1 h / 0 °C

2.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

3.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

5.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

5.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

6.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.2: aq. TFA / 3 h / 20 °C

6.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

7.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

8.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

9.1: 1.107 g / PPTS / 20 °C

10.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

10.2: montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

10.3: 86 percent / NaBH₄ / methanol / 0.33 h / 0 - 5 °C

11.1: 98 percent / imidazole DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

12.2: 86 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -78 °C

13.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium borohydride; n-butyllithium; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo026743f

Reference yield:

: 89408-85-5
(S)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

: 385809-15-4
(2S,4RS,6S)-(2-{(2R,6R)-6-[4-benzenesulfonyl-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2-methylheptyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 14 steps

1.1: 89 percent / imidazole; DMAP / CH₂Cl₂; toluene / 16 h / 0 - 20 °C

2.1: CuI / 0 °C

2.2: 84 percent / diethyl ether / 1 h / 0 °C

3.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

4.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

6.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

6.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

7.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.2: aq. TFA / 3 h / 20 °C

7.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

8.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

9.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

10.1: 1.107 g / PPTS / 20 °C

11.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

11.2: montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

11.3: 86 percent / NaBH₄ / methanol / 0.33 h / 0 - 5 °C

12.1: 98 percent / imidazole DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

13.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

13.2: 86 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -78 °C

14.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium borohydride; n-butyllithium; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo026743f