2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

Base Information

Chemical Name:2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester
CAS No.:634151-72-7
Molecular Formula:C₄₁H₆₀O₄Si
Molecular Weight:645.01
Hs Code.:

2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

Synonyms:2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

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Chemical Property of 2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

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Technology Process of 2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

There total 13 articles about 2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl 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: 67.0%

: 634151-73-8
2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-(4-methoxyphenoxy)-but-3-enyl ester

: 634151-72-7
2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: 634151-74-9
(2S,3R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enyl}-3-(4-methoxyphenoxy)-pent-4-en-2-ol

: 634151-72-7
2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

2: 67 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 °C

With pyridine; dmap; ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: 848760-88-3
(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]3-(4-methoxyphenoxy)-pent-4-en-2-ol

: 634151-72-7
2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / DIPEA; TBAI / CH₂Cl₂ / 7 h / 25 °C

2: LiBF₄ / acetonitrile; H₂O / 6 h / 25 °C

3: 408 mg / NaBH₄ / ethanol / 0.33 h / 25 °C

4: 95 percent / TEA / CH₂Cl₂ / 0 - 25 °C

5: 100 percent / 18-crown-6 / acetonitrile / 2.5 h / 80 °C

6: DIBAL-H / hexane; toluene / 1 h / -78 °C

7: 420 mg / tetrahydrofuran; diethyl ether / 48 h / -78 °C

8: 90 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

9: 45 percent / Me₂S; BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -20 °C

10: 66 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

11: 67 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium tetrafluoroborate; ammonium cerium(IV) nitrate; 18-crown-6 ether; dimethylsulfide; TEA; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 7: Brown allylation;
DOI:10.1016/j.tet.2004.12.039