(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

Base Information

Chemical Name:(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester
CAS No.:143842-92-6
Molecular Formula:C₅₆H₇₆O₇Si₂
Molecular Weight:917.386
Hs Code.:

(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

Synonyms:(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

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Chemical Property of (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

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Technology Process of (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

There total 19 articles about (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-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:

: (1S,3R,7S,8S,8aR)-8-((E)-3-Methoxy-allyl)-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1,3-diol

: 143842-92-6
(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature

2: 87 percent / p-TsOH, H₂O / acetone / 2 h / 56 °C

4: 66 percent / Et₃N / 20 h / Ambient temperature

5: 1) s-Bu₃BHLi, 2) H₂O₂ / 1) THF, -78 deg C, 30 min, 2) THF, H₂O, to r.t.

6: KOH / methanol / 2 h / 60 °C

7: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C

8: VO(acac)2, tert-butylhydroperoxide / CH₂Cl₂ / 3 h / 0 °C

9: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; potassium hydroxide; bis(acetylacetonate)oxovanadium; water; dihydrogen peroxide; L-Selectride; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00052a029

Reference yield:

: 143842-75-5
(3R,5S,8S)-3-Benzyloxy-8-methyl-1-oxa-spiro[4.5]dec-6-en-2-ol

: 143842-92-6
(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 1) KOtBu / 1) THF, 1 h, r.t., 2) THF, r.t., 1 h

2: 92 percent / 48 h / 130 °C

3: 1) disiamylborane, BH₃*SMe₂, 2) 30percent H₂O₂ / 1) THF, r.t., 30 min, 2) MeOH

4: 84 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.05 h / -30 °C

5: Me₂AlCl, MeOH / CH₂Cl₂; hexane / 0.5 h / -40 deg C to r.t.

6: 99.4 percent / tetrahydrofuran / 2 h / Ambient temperature

7: 64 percent / NH₃ liq., Li / tetrahydrofuran / 1 h

8: 1) KOtBu / 1) THF, r.t., 1 h, 2) THF, r.t., 15 min

9: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

10: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature

11: 87 percent / p-TsOH, H₂O / acetone / 2 h / 56 °C

13: 66 percent / Et₃N / 20 h / Ambient temperature

14: 1) s-Bu₃BHLi, 2) H₂O₂ / 1) THF, -78 deg C, 30 min, 2) THF, H₂O, to r.t.

15: KOH / methanol / 2 h / 60 °C

16: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C

17: VO(acac)2, tert-butylhydroperoxide / CH₂Cl₂ / 3 h / 0 °C

18: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; potassium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; water; dihydrogen peroxide; dimethylaluminum chloride; bis-(1,2-dimethylpropyl)borane; lithium; L-Selectride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00052a029

Reference yield:

: 143842-76-6
(1S,4S)-1-((R)-2-Benzyloxy-but-3-enyl)-4-methyl-cyclohex-2-enol

: 143842-92-6
(S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 92 percent / 48 h / 130 °C

2: 1) disiamylborane, BH₃*SMe₂, 2) 30percent H₂O₂ / 1) THF, r.t., 30 min, 2) MeOH

3: 84 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.05 h / -30 °C

4: Me₂AlCl, MeOH / CH₂Cl₂; hexane / 0.5 h / -40 deg C to r.t.

5: 99.4 percent / tetrahydrofuran / 2 h / Ambient temperature

6: 64 percent / NH₃ liq., Li / tetrahydrofuran / 1 h

7: 1) KOtBu / 1) THF, r.t., 1 h, 2) THF, r.t., 15 min

8: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

9: pyridine, 4-(N,N-dimethylamino)pyridine / Ambient temperature

10: 87 percent / p-TsOH, H₂O / acetone / 2 h / 56 °C

12: 66 percent / Et₃N / 20 h / Ambient temperature

13: 1) s-Bu₃BHLi, 2) H₂O₂ / 1) THF, -78 deg C, 30 min, 2) THF, H₂O, to r.t.

14: KOH / methanol / 2 h / 60 °C

15: 99 percent / imidazole / dimethylformamide / 3 h / 80 °C

16: VO(acac)2, tert-butylhydroperoxide / CH₂Cl₂ / 3 h / 0 °C

17: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; potassium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; water; dihydrogen peroxide; dimethylaluminum chloride; bis-(1,2-dimethylpropyl)borane; lithium; L-Selectride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00052a029