(2S,3R)-3-pentyloxirane-2-carbaldehyde

Base Information

• Chemical Name: (2S,3R)-3-pentyloxirane-2-carbaldehyde
• CAS No.: 110222-66-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.198
• Mol file: 110222-66-7.mol

Synonyms:(2S,3R)-3-pentyloxirane-2-carbaldehyde

Chemical Property of (2S,3R)-3-pentyloxirane-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-pentyloxirane-2-carbaldehyde

There total 12 articles about (2S,3R)-3-pentyloxirane-2-carbaldehyde 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: 85.0%

(2R,3R)-2,3-epoxy-1-octanol (97589-09-8) → (2S,3R)-3-pentyloxirane-2-carbaldehyde (110222-66-7,113973-12-9)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane; for 0.75h; Ambient temperature;

Reference yield:

(E)-1-iodooct-1-en-3-ol (39178-65-9) → (2S,3R)-3-pentyloxirane-2-carbaldehyde (110222-66-7,113973-12-9)

Guidance literature:

Multi-step reaction with 6 steps

1: tBuOOH, Ti(OiPr)4, D-(-)-diisopropyl tartrate / CH₂Cl₂

2: 100 percent / Ni(dppp)Cl₂ / diethyl ether / 3 h / Ambient temperature; addition at 0 deg C

3: 75 percent / tBuOOH, Ti(OiPr)4, L-(+)-diisopropyl tartrate, molecular sieves 4A / CH₂Cl₂ / 20 h / -20 °C

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: ⁿBu₄NF / tetrahydrofuran / 1 h / 0 °C

6: ozonolysis

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; D-(-)-diisopropyl tartrate; triethylamine; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)80846-1

Reference yield:

(S)-(E)-(+)-1-Iodo-1-octen-3-ol (39647-93-3) → (2S,3R)-3-pentyloxirane-2-carbaldehyde (110222-66-7,113973-12-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / Ni(dppp)Cl₂ / diethyl ether / 3 h / Ambient temperature; addition at 0 deg C

2: 75 percent / tBuOOH, Ti(OiPr)4, L-(+)-diisopropyl tartrate, molecular sieves 4A / CH₂Cl₂ / 20 h / -20 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: ⁿBu₄NF / tetrahydrofuran / 1 h / 0 °C

5: ozonolysis

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylamine; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)80846-1

upstream raw materials:

(2R,3R)-2-Pentyl-3-vinyl-oxirane

(2R,3R)-2,3-epoxy-1-octanol

(E)-1-iodooct-1-en-3-ol

(S)-(E)-(+)-1-Iodo-1-octen-3-ol

Downstream raw materials:

(10E,12R,13R)-1-tert-Butyldiphenylsilyloxy-12,13-epoxyoctadec-10-en-9-one

trans-4,5-epoxy-(E)-2-decenal

(-) 4-hydroxy-2-nonenal

(S)-4-[(Z)-7-(4-Methoxy-benzyloxy)-hept-2-enyl]-5-[1-((2R,3R)-3-pentyl-oxiranyl)-meth-(E)-ylidene]-cyclopent-2-enone