(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

Base Information

Chemical Name:(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester
CAS No.:87326-74-7
Molecular Formula:C₁₈H₂₁F₃O₉S
Molecular Weight:470.421
Hs Code.:

Synonyms:(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

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Technology Process of (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

There total 12 articles about (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl 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:

: 358-23-6
trifluoromethylsulfonic anhydride

: 87326-73-6
(S)-methyl 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyacetate

: 87326-74-7
(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

Guidance literature:: With pyridine; In dichloromethane; at -10 ℃; for 1h;
DOI:10.1016/0008-6215(84)85281-7

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 87326-74-7
(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

2: pyridine; DMAP / 20 °C

3: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

4: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

5: aq. NaOH / methanol / 20 °C

6: 44 g / KHCO₃ / dimethylformamide / 20 °C

7: pyridine / CH₂Cl₂ / 1 h / -10 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390009

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 87326-74-7
(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: aq. AcOH / 20 h / 20 - 40 °C

2: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

3: pyridine; DMAP / 20 °C

4: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

5: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

6: aq. NaOH / methanol / 20 °C

7: 44 g / KHCO₃ / dimethylformamide / 20 °C

8: pyridine / CH₂Cl₂ / 1 h / -10 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390009