2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

Base Information

• Chemical Name: 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran
• CAS No.: 158800-18-1
• Molecular Formula: C₅₃H₆₆O₄Si₂
• Molecular Weight: 823.276
• Mol file: 158800-18-1.mol

Synonyms:2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

Chemical Property of 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran

There total 11 articles about 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran 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:

tert-butylchlorodiphenylsilane (58479-61-1) → 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran (158800-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

2: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

3: 1.) t-BuLi, 2.) n-Bu₃SnCl, 3.) Pd(PPh₃)4

With pyridine; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tert.-butyl lithium; silver nitrate; In dichloromethane; acetone;

DOI:10.1021/ja00091a004

Reference yield:

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester (135236-80-5,135236-82-7) → 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran (158800-18-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HMPA, NaN(SiMe₃)2 / 1.) THF, from -78 deg C to RT, 1.5 h, 2.) THF, from -78 to -30 deg C, 4 h

2: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 24 °C

3: 95 percent / pyridine, AgNO₃ / CH₂Cl₂ / 6 h / Ambient temperature

4: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

5: 1.) t-BuLi, 2.) n-Bu₃SnCl, 3.) Pd(PPh₃)4

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; silver nitrate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja00091a004

Reference yield:

tert-Butyl-[(Z)-(R)-((1E,3E)-1-hexa-1,3-dien-5-ynyl)-non-3-enyloxy]-diphenyl-silane (157394-82-6) → 2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-6-<7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-ynyl>-2,3-dihydro-4H-pyran (158800-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / AgNO₃, NBS / acetone / 1 h / 24 °C

2: 1.) t-BuLi, 2.) n-Bu₃SnCl, 3.) Pd(PPh₃)4

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyltin chloride; tert.-butyl lithium; silver nitrate; In acetone;

DOI:10.1021/ja00091a004

upstream raw materials:

1-bromo-7(R)-<(tert-butyldiphenylsilyl)oxy>-3(E),5(E),9(Z)-pentadecatrien-1-yne

2(R)-methoxy-4(R)-<(tert-butyldiphenylsilyl)oxy>-2,3-dihydro-4H-pyran

Toluene-4-sulfonic acid (2R,3S)-5-hydroxy-2-((Z)-oct-2-enyl)-tetrahydro-furan-3-yl ester

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(1Z,3E,5E,9Z)-(R)-7-(tert-butyl-diphenyl-silanyloxy)-pentadeca-1,3,5,9-tetraenyl]-2-methoxy-3,4-dihydro-2H-pyran

3(S),12(R)-bis<(tert-butyldiphenylsilyl)oxy>-5(S)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetranoic δ-lactone

2(R)-methoxy-4(S)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<7(R)-<(tert-butyldiphenylsilyl)oxy>-1(Z),3(E),5(E),9(Z)-pentadecatetraen-1-yl>tetrahydropyran

(6Z,8E,10E,14Z)-(3S,5S,12R)-3,12-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester