(-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester

Base Information

• Chemical Name: (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester
• CAS No.: 689277-82-5
• Molecular Formula: C₃₈H₆₄O₇SSi₃
• Molecular Weight: 749.244

Synonyms:(-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester

Chemical Property of (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester

There total 6 articles about (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester 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: 81.0%

4-(tert-butyldimethylsilyloxy)-3-methoxyphenyol chlorothionoformate (689277-81-4) + (-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol (689277-80-3) → (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester (689277-82-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol049878b

Reference yield:

O-tert-butyldimethylsilylvanillin (69404-94-0) → (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester (689277-82-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 1.33 h / -78 - 0 °C

1.2: CH₂Cl₂ / 2 h / -78 - 0 °C

1.3: H₂O₂ / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.2

2.1: 3.11 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3.1: 77 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

4.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol049878b

Reference yield:

formic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl ester → (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester (689277-82-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 4.06 g / K₂CO₃ / methanol / 0.17 h / 25 °C

2: DBU / CH₂Cl₂ / 0.33 h / 0 °C

3: 81 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1021/ol049878b

upstream raw materials:

4-(tert-butyldimethylsilyloxy)-3-methoxyphenyol chlorothionoformate

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

O-tert-butyldimethylsilylvanillin

4-tert-butyldimethylsilyloxy-3-methoxyphenol

Downstream raw materials:

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

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

(8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-oxolignano-9,9'-lactone

conidendrin

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