(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:146518-11-8
Molecular Formula:C₃₆H₅₂N₂O₅SSi
Molecular Weight:652.971
Hs Code.:

(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Synonyms:(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 18 articles about (1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl 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: 87.0%

: 120040-87-1
methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 146518-11-8
(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: In toluene; at 100 ℃; for 16h;
DOI:10.1021/ja00059a024

Reference yield:

: 120143-05-7
(3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene

: 146518-11-8
(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT

2: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

3: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

4: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

5: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

6: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

7: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

8: CrCl₂ / tetrahydrofuran / 3 h / 0 °C

9: 76 percent / 10percent TlOH, Pd(PPh₃)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C

10: 64 percent / BHT / toluene / 16 h / 150 °C

11: K₂CO₃ / methanol / Ambient temperature

12: 81 percent / imidazole / dimethylformamide / 1 h / 25 °C

13: 87 percent / toluene / 16 h / 100 °C

With 1H-imidazole; chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; dimethylsulfide; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00059a024

Reference yield:

: 120040-77-9
(2R,3S)-3-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde

: 146518-11-8
(1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

2: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

3: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

4: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

5: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

6: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

7: CrCl₂ / tetrahydrofuran / 3 h / 0 °C

8: 76 percent / 10percent TlOH, Pd(PPh₃)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C

9: 64 percent / BHT / toluene / 16 h / 150 °C

10: K₂CO₃ / methanol / Ambient temperature

11: 81 percent / imidazole / dimethylformamide / 1 h / 25 °C

12: 87 percent / toluene / 16 h / 100 °C

With 1H-imidazole; chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00059a024