[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

Base Information

Chemical Name:[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene
CAS No.:443283-32-7
Molecular Formula:C₂₉H₅₂O₇Si
Molecular Weight:540.813
Hs Code.:

Synonyms:[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

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Chemical Property of [3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

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Technology Process of [3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

There total 10 articles about [3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene 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: 97.0%

: 107-30-2
chloromethyl methyl ether

: 443283-16-7
[3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol

: 443283-32-7
[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

Guidance literature:: With N-ethyl-N,N-diisopropylamine; for 96h;
DOI:10.1021/jo016413f

Reference yield:

: 443283-14-5
[3R,4R,5R,6R]-4-[(tert-butyldimethylsilyl)oxy]-6-[(3,4-dimethoxybenzyl)oxy]-3,5-dimethylhept-1-ene

: 443283-32-7
[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran / 8 h / pH 7

2: 94 percent / NaIO₄ / tetrahydrofuran / 1.5 h / 23 °C / pH 7

3: 76 percent / chromium(II) chloride; iodotrimethylsilane / tetrahydrofuran / 7 h / -45 °C

4: 97 percent / N,N-diisopropylethyl amine / 96 h

With chromium dichloride; sodium periodate; trimethylsilyl iodide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; In tetrahydrofuran; acetone; 3: Takai reaction;
DOI:10.1021/jo016413f

Reference yield:

: 27372-03-8,51898-35-2,51898-36-3,63647-69-8,78088-27-4,78088-28-5,86853-34-1,92282-67-2,86853-33-0
ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate

: 443283-32-7
[3S,4R,5R,6S,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxy-4-[(methoxymethyl)oxy]non-1-ene

Guidance literature:: Multi-step reaction with 10 steps

1: 94 percent / lithium aluminum hydride / diethyl ether / 1 h

2: 84 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

3: 98 percent / DIBAL-H / CH₂Cl₂ / 2.5 h / 0 °C

4: 9.8 g / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

5: 9.98 g / toluene / -78 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -40 °C

7: 98 percent / N-methylmorpholine N-oxide / osmium tetroxide / acetone; tetrahydrofuran / 8 h / pH 7

8: 94 percent / NaIO₄ / tetrahydrofuran / 1.5 h / 23 °C / pH 7

9: 76 percent / chromium(II) chloride; iodotrimethylsilane / tetrahydrofuran / 7 h / -45 °C

10: 97 percent / N,N-diisopropylethyl amine / 96 h

With 2,6-dimethylpyridine; chromium dichloride; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl iodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; benzene; 4: Swern oxidation / 9: Takai reaction;
DOI:10.1021/jo016413f