((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol

Base Information

• Chemical Name: ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol
• CAS No.: 174198-67-5
• Molecular Formula: C₂₄H₃₆O₆
• Molecular Weight: 420.546

Synonyms:((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol

Chemical Property of ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol

There total 19 articles about ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol 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: 98.0%

(E)-5-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-3-methyl-pent-2-en-1-ol (174198-81-3) → ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol (174198-67-5)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; at -23 ℃;

DOI:10.1016/0040-4039(95)02132-9

Reference yield:

(E)-6-acetoxy-4-methyl-4-hexenal (35334-60-2) → ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol (174198-67-5)

Guidance literature:

Multi-step reaction with 19 steps

1: 69 percent / benzene / Heating

2: 84 percent / K₂CO₃ / methanol / 0 deg C to RT

3: 92 percent / TsOH / diethyl ether / 0 deg C to RT

4: 83 percent / DIBAH / toluene / -65 °C

5: 98 percent / t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

6: 92 percent / Ti(O-iPr)4 / CH₂Cl₂ / 0 deg C to RT

7: 86 percent / Dowex (50W-X₂) / methanol / Ambient temperature

8: 1.) t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) CSA / 1.) CH₂Cl₂, -23 deg C, 2.) CH₂Cl₂, RT

9: p-TsOH / acetone / Ambient temperature

10: K₂CO₃ / ethanol / Ambient temperature

11: 100 percent / imidazole / dimethylformamide / Ambient temperature

12: 92 percent / NaH, n-Bu₄NI / tetrahydrofuran / 0 deg C to RT

13: 93 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

14: pyridine; CH₂Cl₂ / -10 °C

15: CuI / diethyl ether / -50 °C

16: 89 percent / O₂, PdCl₂, CuCl / dimethylformamide; H₂O / Ambient temperature

17: 96 percent / NaH / benzene / Ambient temperature

18: 100 percent / DIBAH / toluene / -78 °C

19: 98 percent / t-BuOOH, L-(+)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; Dowex (50W-X₂); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; copper(l) chloride; palladium dichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/0040-4039(95)02132-9

Reference yield:

(2E,6E)-8-Hydroxy-6-methyl-octa-2,6-dienoic acid methyl ester (110965-85-0) → ((2S,3S)-3-{2-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-oxiranyl)-methanol (174198-67-5)

Guidance literature:

Multi-step reaction with 17 steps

1: 92 percent / TsOH / diethyl ether / 0 deg C to RT

2: 83 percent / DIBAH / toluene / -65 °C

3: 98 percent / t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

4: 92 percent / Ti(O-iPr)4 / CH₂Cl₂ / 0 deg C to RT

5: 86 percent / Dowex (50W-X₂) / methanol / Ambient temperature

6: 1.) t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) CSA / 1.) CH₂Cl₂, -23 deg C, 2.) CH₂Cl₂, RT

7: p-TsOH / acetone / Ambient temperature

8: K₂CO₃ / ethanol / Ambient temperature

9: 100 percent / imidazole / dimethylformamide / Ambient temperature

10: 92 percent / NaH, n-Bu₄NI / tetrahydrofuran / 0 deg C to RT

11: 93 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

12: pyridine; CH₂Cl₂ / -10 °C

13: CuI / diethyl ether / -50 °C

14: 89 percent / O₂, PdCl₂, CuCl / dimethylformamide; H₂O / Ambient temperature

15: 96 percent / NaH / benzene / Ambient temperature

16: 100 percent / DIBAH / toluene / -78 °C

17: 98 percent / t-BuOOH, L-(+)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; Dowex (50W-X₂); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; copper(l) chloride; palladium dichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/0040-4039(95)02132-9

upstream raw materials:

(E)-5-[(2R,3S,6S)-3-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-tetrahydro-pyran-2-yl]-3-methyl-pent-2-en-1-ol

(E)-6-acetoxy-4-methyl-4-hexenal

(2E,6E)-8-Hydroxy-6-methyl-octa-2,6-dienoic acid methyl ester

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate

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