(2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran
• CAS No.: 837428-36-1
• Molecular Formula: C₄₂H₆₆O₃Si₂
• Molecular Weight: 675.155
• Mol file: 837428-36-1.mol

Synonyms:(2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran

Chemical Property of (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran

There total 14 articles about (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-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:

(2R,3R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-prop-2-ynyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-((Z)-dodec-2-enyl)-tetrahydro-pyran → (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran (837428-36-1)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo052233k

Reference yield:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) → (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran (837428-36-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 77 percent / NaHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

2.1: NaBH₄ / tetrahydrofuran; propan-2-ol / 3 h / 0 °C

3.1: DMAP / ethanol; various solvent(s) / 14 h / Heating

4.1: 95 percent / PPh₃; DIAD / toluene / 3 h / 20 °C

5.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

5.2: t-BuOK / toluene / 0.83 h / 0 °C

6.1: t-BuOK / toluene / 0 °C

7.1: DIBAL-H / CH₂Cl₂; toluene / 0.58 h / -78 °C

7.2: 75 percent / NaHMDS / CH₂Cl₂; toluene; tetrahydrofuran / 12 h / -78 - 0 °C

8.1: 83 percent / Al₂O₃ / hexane / 24 h / 20 °C

9.1: 81 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 0 °C

10.1: 83 percent / Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 20 h / 20 °C

11.1: imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

12.1: 105 mg / K₂CO₃ / CH₂Cl₂; methanol / 14 h / 20 °C

With pyridine; 1H-imidazole; dmap; aluminum oxide; lithium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; (1S,2R)-(+)-N-methylephedrine; potassium tert-butylate; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; isopropyl alcohol; toluene; 1.1: Horner-Wadsworth-Emmons reaction / 4.1: Mitsunobu reaction / 7.2: Wittig reaction / 9.1: Dess-Martin oxidation;

DOI:10.1021/jo052233k

Reference yield:

(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-8-oxooct-2-enoate (837428-48-5) → (2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{(R)-1-{[tert-butyl(dimethyl)silyl]oxy}prop-2-ynyl}-2-[(Z)-dodec-2-enyl]tetrahydro-2H-pyran (837428-36-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaBH₄ / tetrahydrofuran; propan-2-ol / 3 h / 0 °C

2.1: DMAP / ethanol; various solvent(s) / 14 h / Heating

3.1: 95 percent / PPh₃; DIAD / toluene / 3 h / 20 °C

4.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.2: t-BuOK / toluene / 0.83 h / 0 °C

5.1: t-BuOK / toluene / 0 °C

6.1: DIBAL-H / CH₂Cl₂; toluene / 0.58 h / -78 °C

6.2: 75 percent / NaHMDS / CH₂Cl₂; toluene; tetrahydrofuran / 12 h / -78 - 0 °C

7.1: 83 percent / Al₂O₃ / hexane / 24 h / 20 °C

8.1: 81 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 0 °C

9.1: 83 percent / Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 20 h / 20 °C

10.1: imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

11.1: 105 mg / K₂CO₃ / CH₂Cl₂; methanol / 14 h / 20 °C

With pyridine; 1H-imidazole; dmap; aluminum oxide; lithium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; (1S,2R)-(+)-N-methylephedrine; potassium tert-butylate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; isopropyl alcohol; toluene; 3.1: Mitsunobu reaction / 6.2: Wittig reaction / 8.1: Dess-Martin oxidation;

DOI:10.1021/jo052233k

upstream raw materials:

decyltriphenylphosphonium bromide

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(Z)-dodec-2-enyl]-tetrahydro-2H-pyran-2-carbaldehyde

{(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(Z)-dodec-2-enyl]-tetrahydro-2H-pyran-2-yl}methanol

Downstream raw materials:

(5S)-3-{(2R,8R,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-[(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-dodecyltetrahydro-2H-pyran-2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl}-5-methylfuran-2(5H)-one

(5S)-3-{(2R,8R,11E,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-{(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(E)-dodec-2-en-1-yl]tetrahydro-2H-pyran-2-yl}-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridec-11-en-9-yn-1-yl}-5-methylfuran-2(5H)-one

(2R,3R,6R)-6-{(E)-(R)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-iodo-allyl}-3-{[tert-butyl(diphenyl)silyl]oxy}-2-[(Z)-dodec-2-enyl]-tetrahydro-2H-pyran