(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

Base Information

Chemical Name:(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol
CAS No.:753016-65-8
Molecular Formula:C₃₂H₄₆O₆
Molecular Weight:526.714
Hs Code.:

Synonyms:(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

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Chemical Property of (E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

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Technology Process of (E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

There total 20 articles about (E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol 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: 86.0%

: 77-76-9
2,2-dimethoxy-propane

: 753016-64-7
(E)-(2R,3S,4S,5R,6S)-10-Benzyloxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-1,3,5-triol

: 753016-65-8
(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ol049219z

Reference yield:

: 157733-27-2
(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene

: 753016-65-8
(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 68 percent / PdCl₂[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C

2.1: 96 percent / DIBAL / CH₂Cl₂; hexane / -78 - 45 °C

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: Sn(OTf)2; Et₃N / CH₂Cl₂ / 3 h / -78 °C

4.2: 77 percent / CH₂Cl₂ / 6 h / -78 °C

5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C

5.2: 73 percent / NaBH₄ / tetrahydrofuran; methanol / 48 h / -78 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 86 percent / PPTS / CH₂Cl₂ / 0.5 h / 20 °C

With tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.2: Paterson's stereoselective aldol reaction;
DOI:10.1021/ol049219z

Reference yield:

: 753016-63-6
(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-en-1-ol

: 753016-65-8
(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / Sn(OTf)2; triethylamine

2: Et₂BOMe; NaBH₄

3: TBAF / tetrahydrofuran

4: PPTS

With sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; 1: Swern oxidation;
DOI:10.1016/j.tetlet.2005.07.029