(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-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,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester
CAS No.:90344-20-0
Molecular Formula:C₄₀H₅₈O₅Si
Molecular Weight:646.983
Hs Code.:

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

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

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

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

There total 21 articles about (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-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:

: 80106-30-5
(4E,6E)-octa-4,6-dien-1-ol

: 90344-20-0
(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 18 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

With pyridine; peracetic acid; dmap; sodium amalgam; 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:

: 68823-50-7
methyl (4E,6E)-octa-4,6-dienoate

: 90344-20-0
(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 19 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

With pyridine; peracetic acid; dmap; sodium amalgam; 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:

: 75283-60-2
dimethyl 2-[(2E,4E)-hexa-2,4-dienyl]propanedioate

: 90344-20-0
(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 20 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

With pyridine; peracetic acid; dmap; sodium cyanide; sodium amalgam; 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