<1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>

Base Information

• Chemical Name: <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>
• CAS No.: 135273-88-0
• Molecular Formula: C₂₉H₄₃NO₆
• Molecular Weight: 501.664
• Mol file: 135273-88-0.mol

Synonyms:<1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>

Chemical Property of <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>

There total 9 articles about <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate> 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: 56.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + <3S(E),4S(S)>-3-hex-1-enyl-4-(2-hydroxyheptyl)-2-oxetanone (135273-87-9) → <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate> (135273-88-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; 0 deg C to room temperature;

DOI:10.1016/S0040-4039(00)78809-5

Reference yield:

(E)-1-iodohexene (16644-98-7) → <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate> (135273-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / CuI, n-BuNH₂ / Pd(PPh₃)4 / benzene

2: 1) MeLi / 1) THF, ether, RT, 3.5h, 2) THF, RT

3: 90.4 percent / Zn(Cu/Ag) / methanol; H₂O / 39 h / 45 - 50 °C

4: 73 percent / t-BuOOH, VO(acac)2 / CH₂Cl₂ / 5 h / 0 °C

5: 2) (NH₄)2Ce(NO₃)6 / 1) THF, 2h, 2) EtOH, 2h, buffer solution

6: 1) dicyclohexylcarbodiimide, 2) 4-N,N-dimethylaminopyridine / 1) CH₂Cl₂, 0 deg C, 15 min, 2) DMF, 4h, RT

With tert.-butylhydroperoxide; dmap; copper(l) iodide; ammonium cerium(IV) nitrate; bis(acetylacetonate)oxovanadium; methyllithium; silver; copper; N-butylamine; dicyclohexyl-carbodiimide; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)80728-6

Reference yield:

(S)-2,2-Dimethyl-4-((Z)-pent-1-enyl)-[1,3]dioxolane (61228-98-6) → <1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate> (135273-88-0)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / PtO₂ / methanol / 760 Torr

2: aq. HCl / 3 h

3: 1) SOCl₂, 2) NaIO₄, RuCl₃*3H₂O / 2) CCl₄, 30 min, reflux, 2) aq. CH₃CN, 0 deg C

4: 1) MeLi / 1) THF, ether, RT, 3.5h, 2) THF, RT

5: 90.4 percent / Zn(Cu/Ag) / methanol; H₂O / 39 h / 45 - 50 °C

6: 73 percent / t-BuOOH, VO(acac)2 / CH₂Cl₂ / 5 h / 0 °C

7: 2) (NH₄)2Ce(NO₃)6 / 1) THF, 2h, 2) EtOH, 2h, buffer solution

8: 1) dicyclohexylcarbodiimide, 2) 4-N,N-dimethylaminopyridine / 1) CH₂Cl₂, 0 deg C, 15 min, 2) DMF, 4h, RT

With hydrogenchloride; tert.-butylhydroperoxide; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; ammonium cerium(IV) nitrate; bis(acetylacetonate)oxovanadium; methyllithium; hydrogen; silver; copper; dicyclohexyl-carbodiimide; zinc; platinum(IV) oxide; In methanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)80728-6

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

<3S(E),4S(S)>-3-hex-1-enyl-4-(2-hydroxyheptyl)-2-oxetanone

(E)-1-iodohexene

(S)-(+)-2,2-dimethyl-4-pentyl-1,3-dioxolane

Downstream raw materials:

valilactone