{(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane
• CAS No.: 112775-40-3
• Molecular Formula: C₃₃H₅₂O₅Si
• Molecular Weight: 556.858
• Mol file: 112775-40-3.mol

Synonyms:

Chemical Property of {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane

There total 19 articles about {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane 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: 59.0%

(4R,5S)-5-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (112775-33-4) + ((R)-10-Benzyloxy-undec-7-ynyl)-triphenyl-phosphonium; bromide (112775-39-0) → {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane (112775-40-3,112837-13-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)96138-0

Reference yield:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane (112775-40-3,112837-13-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / LiAlH₄

2: 72 percent / NaH / dimethylformamide

3: 88 percent / Swern oxidation

4: 90 percent / LiCl, i-Pr₂EtN / acetonitrile

5: 100 percent / i-Bu₂AlH

6: t-BuOOH, Ti(OiPr)4, R,R-(+)-diisopropyl L-tartrate

7: 87 percent / imidazole

8: 100 percent / hydrogen / Pd

9: 81 percent / Swern oxidation

10: 59 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; L-(+)-diisopropyl tartrate; hydrogen; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)96138-0

Reference yield:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane (112775-40-3,112837-13-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / Swern oxidation

2: 90 percent / LiCl, i-Pr₂EtN / acetonitrile

3: 100 percent / i-Bu₂AlH

4: t-BuOOH, Ti(OiPr)4, R,R-(+)-diisopropyl L-tartrate

5: 87 percent / imidazole

6: 100 percent / hydrogen / Pd

7: 81 percent / Swern oxidation

8: 59 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; L-(+)-diisopropyl tartrate; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile;

DOI:10.1016/S0040-4039(00)96138-0

upstream raw materials:

(4R,5S)-5-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxiranyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

((R)-10-Benzyloxy-undec-7-ynyl)-triphenyl-phosphonium; bromide

1-(2-Tetrahydropyranyloxy)-7-octyne

1-Bromopentane