(E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol

Base Information

• Chemical Name: (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol
• CAS No.: 184691-06-3
• Molecular Formula: C₃₈H₆₆O₆Si₃
• Molecular Weight: 703.195
• Mol file: 184691-06-3.mol

Synonyms:(E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol

Chemical Property of (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol

There total 6 articles about (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-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: 37.0%

(S)-(Z)-1-((tert-Butyldimethylsilyl)oxy)-3-(tri-n-butylstannyl)-1-butene + (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyraldehyde (184691-05-2) → (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol (184691-06-3)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1021/jo961671b

Reference yield:

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) → (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol (184691-06-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / InCl₃ / ethyl acetate / -78 deg C to room temperature

2: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

3: 90 percent / O₃, Me₂S

4: 37 percent / BF₃*OEt₂

With 2,6-dimethylpyridine; indium(III) chloride; dimethylsulfide; boron trifluoride diethyl etherate; ozone; In dichloromethane; ethyl acetate;

DOI:10.1021/jo961671b

Reference yield:

2-[(tert-butyldiphenylsilyl)oxy]ethanol (138499-16-8) → (E)-(2R,3S,4R,5R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-oct-6-en-4-ol (184691-06-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -78 deg C to room temperature

2: 89 percent / InCl₃ / ethyl acetate / -78 deg C to room temperature

3: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

4: 90 percent / O₃, Me₂S

5: 37 percent / BF₃*OEt₂

With 2,6-dimethylpyridine; indium(III) chloride; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; ozone; dimethyl sulfoxide; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1021/jo961671b

upstream raw materials:

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyraldehyde

(tert-butyldiphenylsilanyloxy)acetaldehyde

2-[(tert-butyldiphenylsilyl)oxy]ethanol

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₄₄H₈₀O₆Si₄

(2R,3R,4R,5R)-2,3,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-hexan-1-ol

(2S,3R,4R,5R)-2,3,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-hexanal