(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

Base Information

Chemical Name:(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone
CAS No.:689277-84-7
Molecular Formula:C₃₂H₅₀O₇Si₂
Molecular Weight:602.916
Hs Code.:

Synonyms:(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

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Chemical Property of (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

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Technology Process of (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

There total 12 articles about (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-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: 77.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 20268-71-7,347359-71-1
(7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone

: 689277-84-7
(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/ol049878b

Reference yield:

: 69404-94-0
O-tert-butyldimethylsilylvanillin

: 689277-84-7
(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / MgBr₂ / diethyl ether / 20 °C

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

2.2: 88 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 71 percent / NaBH₄; KOH / ethanol / 3 h / 0 - 20 °C

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

4.2: 68 percent / N,N-dimethyl-2-imidazolidinone / tetrahydrofuran / -78 - 20 °C

5.1: 55 percent / (CF₃CO₂)2IPh; H₂O / acetonitrile / 0.5 h / 20 °C

6.1: L-Selectride(R) / tetrahydrofuran / 2 h / -78 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; water; L-Selectride; bis-[(trifluoroacetoxy)iodo]benzene; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; hexane; acetonitrile; 2.2: Michael addition;
DOI:10.1039/b513303c

Reference yield:

: 689277-80-3
(-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol

: 689277-84-7
(7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 44 percent / (Me₃Si)3SiH; AIBN / benzene / 4 h / Heating

3: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C

4: 77 percent / imidazole / dimethylformamide / 4 h / 20 °C

With pyridine; 1H-imidazole; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol049878b