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

Base Information

Chemical Name:[3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol
CAS No.:443283-16-7
Molecular Formula:C₂₇H₄₈O₆Si
Molecular Weight:496.76
Hs Code.:

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

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Chemical Property of [3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol

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Technology Process of [3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol

There total 10 articles about [3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-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: 76.0%

: 6044-68-4
3,3-dimethoxyprop-1-ene

: 442899-79-8
[2S,3S,4R,5R]-3-[(tert-butyldimethylsilyl)oxy]-5-[(3,4-dimethoxybenzyl)oxy]-2,4-dimethylhexan-1-al

: 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

: (3R,4S,5R,6R,7R,8R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxy)-3-methoxy-5,7-dimethyl-non-1-en-4-ol

Guidance literature:: With chromium dichloride; trimethylsilyl iodide; at -42 ℃;
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

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

Guidance literature:: Multi-step reaction with 3 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

With chromium dichloride; sodium periodate; trimethylsilyl iodide; 4-methylmorpholine N-oxide; 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

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

Guidance literature:: Multi-step reaction with 9 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

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; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; benzene; 4: Swern oxidation / 9: Takai reaction;
DOI:10.1021/jo016413f