((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

Base Information

• Chemical Name: ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol
• CAS No.: 127665-69-4
• Molecular Formula: C₂₂H₃₀O₃Si
• Molecular Weight: 370.564
• Mol file: 127665-69-4.mol

Synonyms:((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

Chemical Property of ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

There total 6 articles about ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol 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: 96.0%

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4)

Guidance literature:

With titanium(IV) isopropylate; 1-butyl hydroperoxide; 4 A molecular sieve; diethyl D-tartrate; In dichloromethane; at -20 ℃; for 32h;

DOI:10.1021/ja00167a068

Reference yield: 75.0%

C30H43NO4SSi (1438399-34-8) → ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 0 - 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201201332

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → ((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene / 80 °C

2: diisobutylaluminium hydride / diethyl ether

3: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; In diethyl ether; benzene;

DOI:10.1016/j.tetlet.2012.02.049

upstream raw materials:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

ethyl (4S)-5-(((tert-butyldiphenyl)silyl)oxy)-4-methyl-2(E)-pentenoate

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate

Downstream raw materials:

tert-Butyl-[(R)-2-((2R,3S)-3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

Toluene-4-sulfonic acid (2R,3R)-3-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-oxiranylmethyl ester

tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

(3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol