Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester

Base Information

• Chemical Name: Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester
• CAS No.: 936573-19-2
• Molecular Formula: C₄₁H₅₂O₇
• Molecular Weight: 656.86

Synonyms:

Chemical Property of Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester

There total 28 articles about Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl 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:

ethyl (2E,4S,5R)-5,6-isopropylidenedioxy-4-methyl-2-hexenoate (155433-68-4) → Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester (936573-19-2)

Guidance literature:

Multi-step reaction with 21 steps

1: DIBAL / hexane; CH₂Cl₂ / -78 °C

2: Ti(O-Pr-i)4, (-)-diethyl tartrate, t-BuOOH / CH₂Cl₂ / -23 °C

3: diethyl ether / -40 - -23 °C

4: imidazole / dimethylformamide / 0 °C

5: NaH / dimethylformamide; tetrahydrofuran / 23 °C

6: AcOH, H₂O / ethanol / 23 °C

7: pyridine / 0 °C

8: K₂CO₃ / methanol / 0 °C

9: n-BuLi / tetrahydrofuran / 23 °C

10: NaH / dimethylformamide; tetrahydrofuran / 23 °C

11: CuCl₂, CuO / acetone; H₂O / Heating

12: NaBH₄ / ethanol / -30 °C

13: i-Pr₂NEt / CH₂Cl₂ / 23 °C

14: n-Bu₄NF / tetrahydrofuran / 23 °C

15: I₂, PPh₃, imidazole / benzene / 10 °C

16: acetonitrile / 90 °C

17: 44 percent / NaN(TMS)2 / toluene / -78 - -23 °C

18: H₂ / Pd/C / ethanol / 23 °C

19: HCl / methanol; H₂O / 23 °C

20: pyridine / 80 °C

21: 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; (-)-diethyl tartrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(II) oxide; copper dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)61370-9

Reference yield:

(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol (71565-21-4) → Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester (936573-19-2)

Guidance literature:

Multi-step reaction with 23 steps

1: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) -78 deg C; 2.) -78 deg C to RT

2: t-BuOK / 2-methyl-propan-2-ol / -78 °C

3: DIBAL / hexane; CH₂Cl₂ / -78 °C

4: Ti(O-Pr-i)4, (-)-diethyl tartrate, t-BuOOH / CH₂Cl₂ / -23 °C

5: diethyl ether / -40 - -23 °C

6: imidazole / dimethylformamide / 0 °C

7: NaH / dimethylformamide; tetrahydrofuran / 23 °C

8: AcOH, H₂O / ethanol / 23 °C

9: pyridine / 0 °C

10: K₂CO₃ / methanol / 0 °C

11: n-BuLi / tetrahydrofuran / 23 °C

12: NaH / dimethylformamide; tetrahydrofuran / 23 °C

13: CuCl₂, CuO / acetone; H₂O / Heating

14: NaBH₄ / ethanol / -30 °C

15: i-Pr₂NEt / CH₂Cl₂ / 23 °C

16: n-Bu₄NF / tetrahydrofuran / 23 °C

17: I₂, PPh₃, imidazole / benzene / 10 °C

18: acetonitrile / 90 °C

19: 44 percent / NaN(TMS)2 / toluene / -78 - -23 °C

20: H₂ / Pd/C / ethanol / 23 °C

21: HCl / methanol; H₂O / 23 °C

22: pyridine / 80 °C

23: 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(II) oxide; copper dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)61370-9

Reference yield:

{(2R,3R)-3-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-oxiranyl}-methanol (936495-17-9) → Acetic acid (1S,2R,3S,4S)-3-acetoxy-6-((3S,4R,5S,6S)-4,6-dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-2,4-dimethyl-1-(2-trityloxy-ethyl)-hexyl ester (936573-19-2)

Guidance literature:

Multi-step reaction with 19 steps

1: diethyl ether / -40 - -23 °C

2: imidazole / dimethylformamide / 0 °C

3: NaH / dimethylformamide; tetrahydrofuran / 23 °C

4: AcOH, H₂O / ethanol / 23 °C

5: pyridine / 0 °C

6: K₂CO₃ / methanol / 0 °C

7: n-BuLi / tetrahydrofuran / 23 °C

8: NaH / dimethylformamide; tetrahydrofuran / 23 °C

9: CuCl₂, CuO / acetone; H₂O / Heating

10: NaBH₄ / ethanol / -30 °C

11: i-Pr₂NEt / CH₂Cl₂ / 23 °C

12: n-Bu₄NF / tetrahydrofuran / 23 °C

13: I₂, PPh₃, imidazole / benzene / 10 °C

14: acetonitrile / 90 °C

15: 44 percent / NaN(TMS)2 / toluene / -78 - -23 °C

16: H₂ / Pd/C / ethanol / 23 °C

17: HCl / methanol; H₂O / 23 °C

18: pyridine / 80 °C

19: 23 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(II) oxide; copper dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)61370-9

upstream raw materials:

acetic anhydride

(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

((3R,4S,5S,6S)-4,6-Dimethyl-2,8-dioxa-bicyclo[3.2.1]oct-3-yl)-methanol

(3R,4S,5S,6S)-4,6-Dimethyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carbaldehyde

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