Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-,(2R,3R)-rel-(9CI)

Base Information

• Chemical Name: Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-,(2R,3R)-rel-(9CI)
• CAS No.: 794513-01-2
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 794513-01-2.mol

Synonyms:Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-, (2R,3R)-rel- (9CI)

Chemical Property of Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-,(2R,3R)-rel-(9CI)

Chemical Property:

• Boiling Point: 323.9±17.0 °C(Predicted)
• PKA: 14.44±0.10(Predicted)
• PSA: 41.99000
• Density: 1.120±0.06 g/cm3(Predicted)
• LogP: 1.35300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-,(2R,3R)-rel-(9CI)

There total 18 articles about Oxiranemethanol,3-methyl-3-[(phenylmethoxy)methyl]-,(2R,3R)-rel-(9CI) 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: 93.0%

(2E) 1-benzyloxy-2-methyl-2-buten-4-ol (62311-52-8) → (2S,3R)-(3-benzyloxymethyl-3-methyl-oxiranyl)-methanol (332888-38-7,794513-01-2)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate; In dichloromethane; at -23 - -20 ℃; for 15h;

DOI:10.1021/jo005732o

Reference yield: 88.0%

((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranylmethoxy)-triisopropyl-silane → ((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-methanol (794513-01-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ja0469075

Reference yield:

3-methyl-1-triisopropylsiloxy-2-butene (223906-15-8) → ((2S,3S)-3-Benzyloxymethyl-3-methyl-oxiranyl)-methanol (794513-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 35 percent / SeO₂; tBuOOH / CH₂Cl₂; toluene / 48 h

2.1: 75 percent / mCPBA / CH₂Cl₂ / 3 h / 0 °C

3.1: NaH / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C

3.2: 90 percent / tetrabutylammonium iodide / tetrahydrofuran; dimethylsulfoxide / 60 °C

4.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran

With tert.-butylhydroperoxide; selenium(IV) oxide; tetrabutyl ammonium fluoride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/ja0469075

upstream raw materials:

(2E) 1-benzyloxy-2-methyl-2-buten-4-ol

(E)-methyl 4-hydroxy-3-methylbut-2-enoate

methyl (E)-3-formylcrotonate

4-benzyloxy-3-methylbut-2-enoic acid methyl ester