(-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one

Base Information

• Chemical Name: (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one
• CAS No.: 689277-90-5
• Molecular Formula: C₃₃H₅₂O₇Si₂
• Molecular Weight: 616.943
• Mol file: 689277-90-5.mol

Synonyms:(-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one

Chemical Property of (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one

There total 5 articles about (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one 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:

t-butyldimethylsiyl triflate (69739-34-0) → (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one (689277-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.45 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

3: 88 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

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

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1021/ol049878b

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one (689277-90-5)

Guidance literature:

Multi-step reaction with 5 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: 1.45 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3.1: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

4.1: 88 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

5.1: 44 percent / (Me₃Si)3SiH; AIBN / benzene / 4 h / Heating

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1021/ol049878b

Reference yield:

(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol (689277-88-1) → (-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one (689277-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

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

With pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In dichloromethane; benzene;

DOI:10.1021/ol049878b

upstream raw materials:

t-butyldimethylsiyl triflate

3,4-dimethoxy-benzaldehyde

(-)-(2S,5S)-2-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]but-3-en-1-ol

(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

Downstream raw materials:

α-conidendrin monomethyl ether

Arctigenin

(7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone