(2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol

Base Information

• Chemical Name: (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol
• CAS No.: 855282-24-5
• Molecular Formula: C₂₈H₄₂O₅Si
• Molecular Weight: 486.724
• Mol file: 855282-24-5.mol

Synonyms:(2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol

Chemical Property of (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol

There total 7 articles about (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-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: 83.0%

Benzoic acid (1R,2R,3S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-2-methoxymethoxy-4,4-dimethyl-hex-5-enyl ester (855282-57-4) → (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol (855282-24-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 3h;

DOI:10.1021/ja050728l

Reference yield:

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde (937166-57-9) → (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol (855282-24-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

2: 98 percent / NaH / tetrahydrofuran

3: 98 percent / n-BuSH; ZnBr₂ / CH₂Cl₂ / 0.13 h / 20 °C

4: 80 percent / DIPEA / CH₂Cl₂ / 11 h / 20 °C

5: 91 percent / P₂O₅ / CH₂Cl₂ / 3 h / 20 °C

6: 83 percent / K₂CO₃ / methanol / 3 h / 20 °C

With n-butanethiol; phosphorus pentoxide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja050728l

Reference yield:

(2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol (937166-60-4) → (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol (855282-24-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

2: 90 percent / ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

3: 98 percent / NaH / tetrahydrofuran

4: 98 percent / n-BuSH; ZnBr₂ / CH₂Cl₂ / 0.13 h / 20 °C

5: 80 percent / DIPEA / CH₂Cl₂ / 11 h / 20 °C

6: 91 percent / P₂O₅ / CH₂Cl₂ / 3 h / 20 °C

7: 83 percent / K₂CO₃ / methanol / 3 h / 20 °C

With oxalyl dichloride; n-butanethiol; phosphorus pentoxide; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja050728l

upstream raw materials:

Benzoic acid (1R,2R,3S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-2-methoxymethoxy-4,4-dimethyl-hex-5-enyl ester

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde

(2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol

(4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene

Downstream raw materials:

(((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane