Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester
• CAS No.: 200264-96-6
• Molecular Formula: C₄₂H₆₀O₆Si₂
• Molecular Weight: 717.106

Synonyms:Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

Chemical Property of Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

There total 17 articles about Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester 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: 80.0%

chloro-trimethyl-silane (75-77-4) + Acetic acid (1R,2R,4S,5R,6S,8S,10R,11R)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-10-hydroxy-2-methyl-10-phenylethynyl-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-97-7) → Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-96-6)

Guidance literature:

With 1H-imidazole; In dichloromethane;

DOI:10.1021/ja972279y

Reference yield: 43.0%

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + Acetic acid (1R,2R,4S,5R,6S,8S,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-95-5) + lithium phenylacetylide (4440-01-1) → Acetic acid (1R,2R,4S,5R,6S,8S,10R,11R)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-10-hydroxy-2-methyl-10-phenylethynyl-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-97-7) + Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-96-6)

Guidance literature:

Acetic acid (1R,2R,4S,5R,6S,8S,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester; lithium phenylacetylide; With lithium bromide; In tetrahydrofuran; at -78 ℃;

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In tetrahydrofuran;

DOI:10.1021/ja972279y

Reference yield:

(S)-5-((R)-1-Benzyloxy-allyl)-dihydro-furan-2-one (116386-71-1) → Acetic acid (1R,2R,4S,5R,6S,8S,10R,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester (200264-96-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: LDA / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 98 percent / tetrahydrofuran

3.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

4.1: 100 percent / NaBH₄ / methanol / 0 °C

5.1: 100 percent / m-chloroperoxybenzoic acid / tetrahydrofuran / 0 °C

6.1: 96 percent / DMAP; pyridine

7.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C

8.1: H₂ / Pd/C / ethyl acetate / 2534.03 Torr

8.2: tetrahydrofuran / Heating

9.1: 98 percent / DMAP; pyridine / 0 °C

10.1: 93 percent / SeO₂; t-BuO₂H / CH₂Cl₂

11.1: 92 percent / MnO₂ / CH₂Cl₂

12.1: 96 percent / CuCN / diethyl ether / -60 °C

13.1: LiBr / tetrahydrofuran / -78 °C

13.2: 33 percent / tetrahydrofuran

14.1: 80 percent / imidazole / CH₂Cl₂

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Reduction / 5.1: Oxidation / 6.1: Acetylation / 7.1: Cycloaddition / 8.1: Hydrogenation / 8.2: Wittig olefination / 9.1: Acetylation / 10.1: Oxidation / 11.1: Oxidation / 12.1: Addition / 13.1: Addition / 13.2: silylation / 14.1: silylation;

DOI:10.1021/ja972279y

upstream raw materials:

chloro-trimethyl-silane

Acetic acid (1R,2R,4S,5R,6S,8S,10R,11R)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-10-hydroxy-2-methyl-10-phenylethynyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

Acetic acid (1R,2R,4S,5R,6S,8S,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-yl ester

Downstream raw materials:

C₄₀H₆₀O₅Si₂

resiniferinol-9,13,14-ortho-phenylacetate

Benzoic acid (2S,3aR,6aS,7R,8S,10R,10aR,10bS)-8-acetyl-7,8,10a-trihydroxy-2,10-dimethyl-3-oxo-3a-trimethylsilanyloxy-1,2,3,3a,4,6a,7,8,9,10,10a,10b-dodecahydro-benzo[e]azulen-5-ylmethyl ester

Benzoic acid (2S,3aS,3bR,4R,5aS,8aR,8bS,11aR)-5a-acetyl-3b-hydroxy-2,4-dimethyl-1,7-dioxo-11a-trimethylsilanyloxy-1,2,3,3a,3b,4,5,5a,8a,8b,11,11a-dodecahydro-6,8-dioxa-indeno[5,4-e]azulen-10-ylmethyl ester

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