4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

Base Information

Chemical Name:4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester
CAS No.:943226-87-7
Molecular Formula:C₄₈H₈₀O₈Si
Molecular Weight:813.244
Hs Code.:

4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

Synonyms:4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

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Chemical Property of 4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

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Technology Process of 4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

There total 39 articles about 4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-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: 100.0%

: 943226-73-1
10a,11a-dimethyl-2-pent-3-enyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

: 943226-84-4
4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid

: 943226-87-7
4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

Guidance literature:: 4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 40 ℃; for 2h;

10a,11a-dimethyl-2-pent-3-enyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol; With dmap; In toluene; at 40 ℃; for 2h; Further stages.;
DOI:10.1021/ol0707970

Reference yield:

: 943226-56-0
(4aS,6R,7S,8R,8aS)-2,2-di-tert-butyl-8-(tert-butyl-diphenyl-silanyloxy)-6-methyl-6-(2-methylallyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

: 943226-87-7
4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 100 percent / NaH / hexamethylphosphoric acid triamide / 0.83 h / 0 °C

2.1: 96 percent / iPr₂NEt / CH₂Cl₂ / -78 °C

3.1: 92 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: 91 percent / 10-camphorsulfonic acid / methanol / 0.08 h / 0 °C

5.1: NaH / 4 h / 20 °C

5.2: 0.5 h / 20 °C

6.1: 0.046 g / n-Bu₃SnH; AIBN / benzene / 1.5 h / Heating

7.1: 100 percent / TiCl₄; TMEDA; Zn dust / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 2 h

8.1: 0.038 g / Grubbs second generation catalyst / benzene / 36 h / Heating

9.1: dimethyl dioxirane / CH₂Cl₂; acetone / -78 - 0 °C

9.2: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

10.1: 80 percent / PPTS; pyridine / chlorobenzene / 48 h / Heating

11.1: 76 percent / H₂ / PtO₂*H₂O / hexane; ethyl acetate / 5.5 h / 760.05 Torr

12.1: 94 percent / HF*pyridine / tetrahydrofuran / 1 h / 0 °C

13.1: CH₂Cl₂ / 0.25 h / -78 °C

13.2: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

14.1: CuI / tetrahydrofuran / -78 - 0 °C

14.2: tetrahydrofuran / 2 h / -40 °C

15.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

16.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

17.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

17.2: tetrahydrofuran / 0.05 h / 20 °C

18.1: 0.0012 g / TBAF / tetrahydrofuran / 0.5 h / 20 °C

19.1: 2,4,6-trichlorobenzoyl chloride; NEt₃ / tetrahydrofuran / 2 h / 40 °C

19.2: 100 percent / DMAP / toluene / 2 h / 40 °C

With pyridine; lead(IV) acetate; dmap; copper(l) iodide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; platinum(IV) oxide; lead(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; ethyl acetate; chlorobenzene; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/ol0707970

Reference yield:

: 943226-61-7
5,5-dimethoxypentanoic acid 2,2-di-tert-butyl-6-methyl-6-(2-methylallyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yl ester

: 943226-87-7
4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / TiCl₄; TMEDA; Zn dust / PbCl₂ / CH₂Cl₂; tetrahydrofuran / 2 h

2.1: 0.038 g / Grubbs second generation catalyst / benzene / 36 h / Heating

3.1: dimethyl dioxirane / CH₂Cl₂; acetone / -78 - 0 °C

3.2: 95 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

4.1: 80 percent / PPTS; pyridine / chlorobenzene / 48 h / Heating

5.1: 76 percent / H₂ / PtO₂*H₂O / hexane; ethyl acetate / 5.5 h / 760.05 Torr

6.1: 94 percent / HF*pyridine / tetrahydrofuran / 1 h / 0 °C

7.1: CH₂Cl₂ / 0.25 h / -78 °C

7.2: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

8.1: CuI / tetrahydrofuran / -78 - 0 °C

8.2: tetrahydrofuran / 2 h / -40 °C

9.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

10.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

11.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

11.2: tetrahydrofuran / 0.05 h / 20 °C

12.1: 0.0012 g / TBAF / tetrahydrofuran / 0.5 h / 20 °C

13.1: 2,4,6-trichlorobenzoyl chloride; NEt₃ / tetrahydrofuran / 2 h / 40 °C

13.2: 100 percent / DMAP / toluene / 2 h / 40 °C

With pyridine; lead(IV) acetate; copper(l) iodide; osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; titanium tetrachloride; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; platinum(IV) oxide; lead(II) chloride; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; chlorobenzene; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/ol0707970