Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester
CAS No.:511256-98-7
Molecular Formula:C₂₃H₃₃F₃O₉S
Molecular Weight:542.571
Hs Code.:

Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Synonyms:Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

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Chemical Property of Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

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Technology Process of Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

There total 15 articles about Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl 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: 62.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 511256-97-6
(2S,3R,4aS,6R,7S,8aR)-6-Hydroxymethyl-2-[3-(4-methoxy-benzyloxy)-propyl]-3,4a-dimethyl-octahydro-pyrano[3,2-b]pyran-3,7-diol

: 511256-98-7
Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -65 - 20 ℃;
DOI:10.1021/ol034100w

Reference yield:

: 191593-14-3
4,6-O-di(tert-butyl)silanediyl-D-glucal

: 511256-98-7
Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C

2.2: 95 percent / tetrahydrofuran; pentane / -70 - 20 °C

3.1: dimethyl dioxirane / CH₂Cl₂ / 0.5 h / -65 °C

3.2: 90 percent / CH₂Cl₂ / 0.25 h / -65 °C

4.1: 95 percent / NaH / hexamethylphosphoric acid triamide / 0.5 h / 0 °C

5.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / -65 - 20 °C

6.1: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / 20 °C

7.1: 100 percent / glacial AcOH / methanol; H₂O / 6 h / 0 °C

8.1: NaH / 4 h / 20 °C

8.2: 86 percent / 48 h / 20 °C

9.1: 19.4 mg / n-Bu₃SnH; AIBN / toluene / 2 h / 110 °C

10.1: 100 percent / TiCl₄; TMEDA; Zn / PbCl₂ / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

11.1: 77 percent / [N,N'-(Mes)2-imidazolidin-2-yl]Ru=CHPh(PCy₃)Cl₂ / benzene / 64 h / 80 °C

12.1: dimethyl dioxirane / CH₂Cl₂; acetone / -65 - 0 °C

13.1: 50 mg / DIBAL / CH₂Cl₂; toluene / 0.25 h / -65 °C

14.1: 100 percent / HF*pyridine / tetrahydrofuran / 3 h / 0 °C

15.1: 62 percent / 2,6-lutidine / CH₂Cl₂ / -65 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; pentane; benzene;
DOI:10.1021/ol034100w

Reference yield:

: 511256-93-2
(4aR,6S,7R,8S,8aR)-2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalene-7,8-diol

: 511256-98-7
Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / -65 - 20 °C

2.1: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / 20 °C

3.1: 100 percent / glacial AcOH / methanol; H₂O / 6 h / 0 °C

4.1: NaH / 4 h / 20 °C

4.2: 86 percent / 48 h / 20 °C

5.1: 19.4 mg / n-Bu₃SnH; AIBN / toluene / 2 h / 110 °C

6.1: 100 percent / TiCl₄; TMEDA; Zn / PbCl₂ / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

7.1: 77 percent / [N,N'-(Mes)2-imidazolidin-2-yl]Ru=CHPh(PCy₃)Cl₂ / benzene / 64 h / 80 °C

8.1: dimethyl dioxirane / CH₂Cl₂; acetone / -65 - 0 °C

9.1: 50 mg / DIBAL / CH₂Cl₂; toluene / 0.25 h / -65 °C

10.1: 100 percent / HF*pyridine / tetrahydrofuran / 3 h / 0 °C

11.1: 62 percent / 2,6-lutidine / CH₂Cl₂ / -65 - 20 °C

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/ol034100w