Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

Base Information

Chemical Name:Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester
CAS No.:174198-61-9
Molecular Formula:C₂₂H₃₂O₇S
Molecular Weight:440.558
Hs Code.:

Synonyms:Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

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Chemical Property of Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

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Technology Process of Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

There total 18 articles about Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl 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: 73.0%

: 124-63-0
methanesulfonyl chloride

: 174198-77-7
Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-hydroxy-ethyl ester

: 174198-61-9
Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

Guidance literature:: With triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1016/0040-4039(95)02132-9

Reference yield:

: 35334-60-2
(E)-6-acetoxy-4-methyl-4-hexenal

: 174198-61-9
Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

Guidance literature:: Multi-step reaction with 18 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: 67 percent / acetic acid; H₂O / RT to 100 deg C

17: 73 percent / collidine / CH₂Cl₂ / -78 °C

18: 73 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; Dowex (50W-X₂); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/0040-4039(95)02132-9

Reference yield:

: 110965-85-0
(2E,6E)-8-Hydroxy-6-methyl-octa-2,6-dienoic acid methyl ester

: 174198-61-9
Acetic acid (R)-2-((2S,5S,6R)-5-benzyloxy-6-but-3-enyl-2-methyl-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester

Guidance literature:: Multi-step reaction with 16 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: 67 percent / acetic acid; H₂O / RT to 100 deg C

15: 73 percent / collidine / CH₂Cl₂ / -78 °C

16: 73 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; Dowex (50W-X₂); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/0040-4039(95)02132-9