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

Base Information

• Chemical Name: (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester
• CAS No.: 90344-22-2
• Molecular Formula: C₃₉H₅₄O₅Si
• Molecular Weight: 630.94
• Mol file: 90344-22-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-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:

(4E,6E)-octa-4,6-dien-1-ol (80106-30-5) → (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (90344-22-2)

Guidance literature:

Multi-step reaction with 20 steps

1: 95 percent / pyridine / 15 h / 5 °C

2: 94 percent / NaOMe / methanol / 2 h

3: 75 percent / 40 percent peracetic acid / ethyl acetate / 2 h / -20 - 0 °C

4: 70 percent / benzene / 24 h / 80 °C

5: 1 M lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 deg C, 5 d, -40 deg C, 8 h

7: aluminum amalgam / tetrahydrofuran; H₂O / 3 h

8: 92 percent / NaOMe / methanol / 24 h / 40 °C

9: 100 percent / TsOH / benzene / 72 h / 80 °C / Dean-Stark apparatus

10: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

11: Me₃SiCl, NaI / acetonitrile / 1 h

12: benzene / 3 h / 80 °C / dark

13: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 15 h

14: 1.) 1.6 M n-BuLi / 1.) THF, HMPA, 0 deg C, 30 min; 2.) THF, HMPA, -78 deg C to RT, 4 h

15: HgCl₂, CaCO₃ / acetonitrile; H₂O / 7 h / 80 °C

16: 6 percent sodium amalgam / methanol / 2 h

17: L-Selectride / tetrahydrofuran / 0.5 h / 0 °C

18: DCC, DMAP / CH₂Cl₂ / 24 h

19: 10 percent HCl / tetrahydrofuran / 3 h / 45 °C

20: PCC-Al₂O₃ / CH₂Cl₂ / 8 h

With pyridine; hydrogenchloride; peracetic acid; dmap; sodium amalgam; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; aluminium amalgam; boron trifluoride diethyl etherate; sodium methylate; L-Selectride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; calcium carbonate; sodium iodide; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/ja00325a017

Reference yield:

methyl (4E,6E)-octa-4,6-dienoate (68823-50-7) → (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (90344-22-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 99 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: 95 percent / pyridine / 15 h / 5 °C

3: 94 percent / NaOMe / methanol / 2 h

4: 75 percent / 40 percent peracetic acid / ethyl acetate / 2 h / -20 - 0 °C

5: 70 percent / benzene / 24 h / 80 °C

6: 1 M lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 deg C, 5 d, -40 deg C, 8 h

8: aluminum amalgam / tetrahydrofuran; H₂O / 3 h

9: 92 percent / NaOMe / methanol / 24 h / 40 °C

10: 100 percent / TsOH / benzene / 72 h / 80 °C / Dean-Stark apparatus

11: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

12: Me₃SiCl, NaI / acetonitrile / 1 h

13: benzene / 3 h / 80 °C / dark

14: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 15 h

15: 1.) 1.6 M n-BuLi / 1.) THF, HMPA, 0 deg C, 30 min; 2.) THF, HMPA, -78 deg C to RT, 4 h

16: HgCl₂, CaCO₃ / acetonitrile; H₂O / 7 h / 80 °C

17: 6 percent sodium amalgam / methanol / 2 h

18: L-Selectride / tetrahydrofuran / 0.5 h / 0 °C

19: DCC, DMAP / CH₂Cl₂ / 24 h

20: 10 percent HCl / tetrahydrofuran / 3 h / 45 °C

21: PCC-Al₂O₃ / CH₂Cl₂ / 8 h

With pyridine; hydrogenchloride; peracetic acid; dmap; sodium amalgam; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; aluminium amalgam; boron trifluoride diethyl etherate; sodium methylate; L-Selectride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; calcium carbonate; sodium iodide; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/ja00325a017

Reference yield:

dimethyl 2-[(2E,4E)-hexa-2,4-dienyl]propanedioate (75283-60-2) → (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (90344-22-2)

Guidance literature:

Multi-step reaction with 22 steps

1: 75 percent / sodium cyanide / dimethylsulfoxide / 3 h / 120 °C

2: 99 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / pyridine / 15 h / 5 °C

4: 94 percent / NaOMe / methanol / 2 h

5: 75 percent / 40 percent peracetic acid / ethyl acetate / 2 h / -20 - 0 °C

6: 70 percent / benzene / 24 h / 80 °C

7: 1 M lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 deg C, 5 d, -40 deg C, 8 h

9: aluminum amalgam / tetrahydrofuran; H₂O / 3 h

10: 92 percent / NaOMe / methanol / 24 h / 40 °C

11: 100 percent / TsOH / benzene / 72 h / 80 °C / Dean-Stark apparatus

12: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

13: Me₃SiCl, NaI / acetonitrile / 1 h

14: benzene / 3 h / 80 °C / dark

15: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 15 h

16: 1.) 1.6 M n-BuLi / 1.) THF, HMPA, 0 deg C, 30 min; 2.) THF, HMPA, -78 deg C to RT, 4 h

17: HgCl₂, CaCO₃ / acetonitrile; H₂O / 7 h / 80 °C

18: 6 percent sodium amalgam / methanol / 2 h

19: L-Selectride / tetrahydrofuran / 0.5 h / 0 °C

20: DCC, DMAP / CH₂Cl₂ / 24 h

21: 10 percent HCl / tetrahydrofuran / 3 h / 45 °C

22: PCC-Al₂O₃ / CH₂Cl₂ / 8 h

With pyridine; hydrogenchloride; peracetic acid; dmap; sodium cyanide; sodium amalgam; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; aluminium amalgam; boron trifluoride diethyl etherate; sodium methylate; L-Selectride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; calcium carbonate; sodium iodide; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/ja00325a017

upstream raw materials:

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

(4E,6E)-octa-4,6-dien-1-ol

(S)-2-Methylbutyric acid

methyl (4E,6E)-octa-4,6-dienoate

Downstream raw materials:

(+)-dihydrocompactin