C₄₂H₅₈O₉

Base Information

• Chemical Name: C₄₂H₅₈O₉
• CAS No.: 565226-37-1
• Molecular Formula: C₄₂H₅₈O₉
• Molecular Weight: 706.917
• Mol file: 565226-37-1.mol

Synonyms:

Chemical Property of C₄₂H₅₈O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₂H₅₈O₉

There total 44 articles about C₄₂H₅₈O₉ 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:

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol (106357-30-6) → C42H58O9 (565226-37-1)

Guidance literature:

Multi-step reaction with 29 steps

1.1: 73 percent / KH; 18-crown-6 / 3 h / 25 °C

2.1: OsO₄; NMO / acetone; H₂O / 20 h / 25 °C

3.1: NaIO₄ / acetone; H₂O / 20 h / 25 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / 6 h / -90 - -30 °C

5.1: TsOH / benzene / 14 h / 25 °C

6.1: OsO₄; NMO / acetone; H₂O / 20 h / 25 °C

7.1: NaIO₄ / acetone; H₂O / 1 h / 20 °C

8.1: LiAlH₄ / diethyl ether / 0.25 h / 0 °C

9.1: imidazole / CH₂Cl₂ / 1 h / 25 °C

10.1: H₂ / Raney Ni (W-2) / ethanol / 120 h / 25 °C

11.1: pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

12.1: NaI; NaHCO₃ / butan-2-one / 20 h / 60 °C

13.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C

13.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

15.1: t-BuOK / toluene / 1.5 h / 95 °C

16.1: TBAF / tetrahydrofuran / 10 h / 20 °C

17.1: imidazole / CH₂Cl₂ / 0.25 h / 20 °C

18.1: CSA / CH₂Cl₂ / 1 h / 15 °C

19.1: TBAF / tetrahydrofuran / 3 h / 20 °C

20.1: Jones reagent / acetone / 1.5 h / -30 °C

21.1: diethyl ether / 0.5 h / 0 °C

22.1: DDQ / CH₂Cl₂; H₂O / 0.25 h / 0 °C

23.1: NaOH / methanol / 90 h / 20 °C

24.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 h / 20 °C

24.2: 22 percent Turnov_. / DMAP / tetrahydrofuran; toluene / 20 h / Heating

25.1: aq. HCl / tetrahydrofuran / 140 h / 20 °C

26.1: CSA / CH₂Cl₂ / 0.5 h / 20 °C

27.1: m-CPBA / toluene / 1.5 h / 80 °C

28.1: Dess-Martin periodinane / CH₂Cl₂ / 48 h / 20 °C

29.1: pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; benzene; 15.1: Wittig reaction / 20.1: Jones oxidation;

DOI:10.1016/S0040-4039(03)00955-9

Reference yield:

(S)-2-[(4R,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propan-1-ol (97718-92-8) → C42H58O9 (565226-37-1)

Guidance literature:

Multi-step reaction with 21 steps

1.1: imidazole / CH₂Cl₂ / 1 h / 25 °C

2.1: H₂ / Raney Ni (W-2) / ethanol / 120 h / 25 °C

3.1: pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

4.1: NaI; NaHCO₃ / butan-2-one / 20 h / 60 °C

5.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C

5.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: t-BuOK / toluene / 1.5 h / 95 °C

8.1: TBAF / tetrahydrofuran / 10 h / 20 °C

9.1: imidazole / CH₂Cl₂ / 0.25 h / 20 °C

10.1: CSA / CH₂Cl₂ / 1 h / 15 °C

11.1: TBAF / tetrahydrofuran / 3 h / 20 °C

12.1: Jones reagent / acetone / 1.5 h / -30 °C

13.1: diethyl ether / 0.5 h / 0 °C

14.1: DDQ / CH₂Cl₂; H₂O / 0.25 h / 0 °C

15.1: NaOH / methanol / 90 h / 20 °C

16.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 h / 20 °C

16.2: 22 percent Turnov_. / DMAP / tetrahydrofuran; toluene / 20 h / Heating

17.1: aq. HCl / tetrahydrofuran / 140 h / 20 °C

18.1: CSA / CH₂Cl₂ / 0.5 h / 20 °C

19.1: m-CPBA / toluene / 1.5 h / 80 °C

20.1: Dess-Martin periodinane / CH₂Cl₂ / 48 h / 20 °C

21.1: pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; 7.1: Wittig reaction / 12.1: Jones oxidation;

DOI:10.1016/S0040-4039(03)00955-9

Reference yield:

(2S,3S,4S,5R,6S)-1-Benzyloxy-2,4,6-trimethyl-oct-7-ene-3,5-diol (97674-79-8) → C42H58O9 (565226-37-1)

Guidance literature:

Multi-step reaction with 25 steps

1.1: TsOH / benzene / 14 h / 25 °C

2.1: OsO₄; NMO / acetone; H₂O / 20 h / 25 °C

3.1: NaIO₄ / acetone; H₂O / 1 h / 20 °C

4.1: LiAlH₄ / diethyl ether / 0.25 h / 0 °C

5.1: imidazole / CH₂Cl₂ / 1 h / 25 °C

6.1: H₂ / Raney Ni (W-2) / ethanol / 120 h / 25 °C

7.1: pyridine; DMAP / CH₂Cl₂ / 20 h / 20 °C

8.1: NaI; NaHCO₃ / butan-2-one / 20 h / 60 °C

9.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C

9.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

11.1: t-BuOK / toluene / 1.5 h / 95 °C

12.1: TBAF / tetrahydrofuran / 10 h / 20 °C

13.1: imidazole / CH₂Cl₂ / 0.25 h / 20 °C

14.1: CSA / CH₂Cl₂ / 1 h / 15 °C

15.1: TBAF / tetrahydrofuran / 3 h / 20 °C

16.1: Jones reagent / acetone / 1.5 h / -30 °C

17.1: diethyl ether / 0.5 h / 0 °C

18.1: DDQ / CH₂Cl₂; H₂O / 0.25 h / 0 °C

19.1: NaOH / methanol / 90 h / 20 °C

20.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 h / 20 °C

20.2: 22 percent Turnov_. / DMAP / tetrahydrofuran; toluene / 20 h / Heating

21.1: aq. HCl / tetrahydrofuran / 140 h / 20 °C

22.1: CSA / CH₂Cl₂ / 0.5 h / 20 °C

23.1: m-CPBA / toluene / 1.5 h / 80 °C

24.1: Dess-Martin periodinane / CH₂Cl₂ / 48 h / 20 °C

25.1: pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; Raney Ni (W-2); In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; benzene; 11.1: Wittig reaction / 16.1: Jones oxidation;

DOI:10.1016/S0040-4039(03)00955-9

upstream raw materials:

acetic anhydride

1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

(2RS,3SR)-3-O-benzyl-2-methyl-1,3-butanediol

(2R,3S)-1-Benzyloxymethyloxy-2-methylbutan-3-ol

Refernces