[(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 725268-55-3
• Molecular Formula: C₅₃H₇₄O₇SSi
• Molecular Weight: 883.318

Synonyms:[(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

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Technology Process of [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane

There total 22 articles about [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane 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: 90.0%

1-((E)-(R)-7-Benzenesulfonyl-6-methyl-hept-4-enyloxymethyl)-4-methoxy-benzene (725268-34-8) + [(1R,2R)-3-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-iodomethyl-2-methyl-propoxy]-tert-butyl-dimethyl-silane (725268-33-7) → [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane (725268-55-3)

Guidance literature:

1-((E)-(R)-7-Benzenesulfonyl-6-methyl-hept-4-enyloxymethyl)-4-methoxy-benzene; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

[(1R,2R)-3-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-iodomethyl-2-methyl-propoxy]-tert-butyl-dimethyl-silane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 2h; Further stages.;

DOI:10.1016/j.tet.2004.04.072

Reference yield:

2-((4R,5R)-4,5-Bis-benzyloxy-cyclohex-2-enyl)-ethanol → [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane (725268-55-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 80 percent / p-TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / 5 h / 95 °C

2.1: 92 percent / EtN₃; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: 91 percent / dimethylsulfoxide / 4 h / 60 °C

4.1: 100 percent / KOH / ethanol; H₂O / Heating

5.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 1.5 h / -78 - 0 °C

5.2: 92 percent / LiCl / tetrahydrofuran / 20 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.2: 94 percent / tetrahydrofuran / 6 h / -78 °C

7.1: 91 percent / LiAlH₄ / tetrahydrofuran / 0 °C

8.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

9.1: CH₂Cl₂ / 20 °C

10.1: 872.1 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

11.1: 99 percent / molecular sieves 4 Angstroem; (-)-diethyl tartrate; Ti(O-iPr)4 / t-butyl hydroperoxide / CH₂Cl₂; decane / 4 h / -20 °C

12.1: imidazole; Ph₃P; I₂ / tetrahydrofuran / 1.5 h / 20 °C

13.1: 706.8 mg / Zn; acetic acid / ethanol; CH₂Cl₂ / 2 h / 20 °C

14.1: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

15.1: NMO; OsO₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

16.1: NaIO₄ / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C / pH 7

17.1: 138.2 mg / NaBH₄ / methanol / 0.5 h / 0 °C

18.1: 96 percent / imidazole; Ph₃P; I₂ / benzene / 0.5 h / 20 °C

19.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

19.2: 90 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; potassium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; 4 A molecular sieve; iodine; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; lithium hexamethyldisilazane; zinc; ethyl azide; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; decane; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; benzene; 9.1: Wittig reaction / 11.1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tet.2004.04.072

Reference yield:

(R)-3-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-2-methyl-propionaldehyde → [(E)-(1S,4R)-3-Benzenesulfonyl-1-[(R)-2-((1S,3R,4R)-3,4-bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-9-(4-methoxy-benzyloxy)-4-methyl-non-5-enyloxy]-tert-butyl-dimethyl-silane (725268-55-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: CH₂Cl₂ / 20 °C

2.1: 872.1 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 99 percent / molecular sieves 4 Angstroem; (-)-diethyl tartrate; Ti(O-iPr)4 / t-butyl hydroperoxide / CH₂Cl₂; decane / 4 h / -20 °C

4.1: imidazole; Ph₃P; I₂ / tetrahydrofuran / 1.5 h / 20 °C

5.1: 706.8 mg / Zn; acetic acid / ethanol; CH₂Cl₂ / 2 h / 20 °C

6.1: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

7.1: NMO; OsO₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

8.1: NaIO₄ / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C / pH 7

9.1: 138.2 mg / NaBH₄ / methanol / 0.5 h / 0 °C

10.1: 96 percent / imidazole; Ph₃P; I₂ / benzene / 0.5 h / 20 °C

11.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

11.2: 90 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; iodine; diisobutylaluminium hydride; acetic acid; (-)-diethyl tartrate; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; zinc; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; decane; ethanol; hexane; dichloromethane; water; benzene; 1.1: Wittig reaction / 3.1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tet.2004.04.072

upstream raw materials:

1-((E)-(R)-7-Benzenesulfonyl-6-methyl-hept-4-enyloxymethyl)-4-methoxy-benzene

[(1R,2R)-3-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-iodomethyl-2-methyl-propoxy]-tert-butyl-dimethyl-silane

t-butyldimethylsiyl triflate

4-(p-methoxybenzyloxy)butan-1-ol

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