(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

Base Information

Chemical Name:(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone
CAS No.:877438-34-1
Molecular Formula:C₃₅H₅₄O₆S₂Si₂
Molecular Weight:691.113
Hs Code.:

Synonyms:(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

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Chemical Property of (8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

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Technology Process of (8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

There total 4 articles about (8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone 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: 68.0%

: 877438-38-5
(3R)-3-[(propane-1,3-diyldithio)-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)methyl]butano-4-lactone

: 113931-97-8
4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide

: 877438-34-1
(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

Guidance literature:: (3R)-3-[(propane-1,3-diyldithio)-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)methyl]butano-4-lactone; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
DOI:10.1039/b513303c

Reference yield:

: 877438-30-7
2-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)-1,3-dithiane

: 877438-34-1
(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 88 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 71 percent / NaBH₄; KOH / ethanol / 3 h / 0 - 20 °C

3.1: LDA / tetrahydrofuran / 2 h / -78 °C

3.2: 68 percent / N,N-dimethyl-2-imidazolidinone / tetrahydrofuran / -78 - 20 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; 1.2: Michael addition;
DOI:10.1039/b513303c

Reference yield:

: 877438-36-3
(3R,4R)-3-[(propane-1,3-diyldithio)-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)methyl]-4-[(1R,2S,5R)-2-(1-methylethyl)-5-methyl-1-cyclohexyloxy]butano-4-lactone

: 877438-34-1
(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 71 percent / NaBH₄; KOH / ethanol / 3 h / 0 - 20 °C

2.1: LDA / tetrahydrofuran / 2 h / -78 °C

2.2: 68 percent / N,N-dimethyl-2-imidazolidinone / tetrahydrofuran / -78 - 20 °C

With potassium hydroxide; sodium tetrahydroborate; lithium diisopropyl amide; In tetrahydrofuran; ethanol;
DOI:10.1039/b513303c