(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

Base Information

• Chemical Name: (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol
• CAS No.: 157117-26-5
• Molecular Formula: C₄₁H₅₉NO₃Si
• Molecular Weight: 642.01
• Mol file: 157117-26-5.mol

Synonyms:(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

Chemical Property of (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

There total 16 articles about (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-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: 71.0%

n-tetradecylmagnesium chloride (110220-87-6) + (4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde (220869-71-6) → (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol (157117-26-5) + [(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-methanol + (1S,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -70 - -20 ℃; other reagents: ZnCl₂, CeCl₃, reagent absence;

DOI:10.1016/S0040-4020(98)01104-1

Reference yield: 50.0%

(4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde (220869-71-6) → (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol (157117-26-5) + [(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-methanol + (1S,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

Guidance literature:

With n-tetradecylmagnesium chloride; zinc(II) chloride; In tetrahydrofuran; at -70 - -20 ℃; Yield given; other reagents: BF₃*OEt₂, CeCl₃, reagent absence;

DOI:10.1016/S0040-4020(98)01104-1

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol (157117-26-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) pyridine / 1.) CH₂Cl₂, room temperature, 24 h, 2.) CH₂Cl₂, 0-5 deg C, 5 h

2: 85 percent / pyridine, triethylamine / toluene / 24 h / 110 °C

3: 84 percent / thiophenol, TiCl₄ / CH₂Cl₂ / 1 h / -15 - -10 °C / other reagent: BF₃*OEt₂

4: NaIO₄ / methanol; H₂O / 2 h / 5 - 10 °C

5: 50 percent / ZnCl₂, tetradecylmagnesium chloride / tetrahydrofuran / -70 - -20 °C / other reagents: BF₃*OEt₂, CeCl₃, reagent absence

With pyridine; sodium periodate; titanium tetrachloride; thiophenol; triethylamine; n-tetradecylmagnesium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1016/S0040-4020(98)01104-1

upstream raw materials:

(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole

n-tetradecylmagnesium chloride

(4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde

tert-butylchlorodiphenylsilane

Downstream raw materials:

(1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide

(1R,4'S,5'S)-1-<4'-hydroxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

D-ribo-phytosphingosine