(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

Base Information

Chemical Name:(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester
CAS No.:127646-32-6
Molecular Formula:C₁₇H₁₉F₃O₈S₂
Molecular Weight:472.46
Hs Code.:

Synonyms:(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

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Chemical Property of (S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

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Technology Process of (S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

There total 5 articles about (S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl 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: 94.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 127646-31-5
Phenyl (Methyl 2,3-O-isopropylidene-δ-D-allofuranosid)thiouronate

: 127646-32-6
(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

Guidance literature:: With pyridine; In dichloromethane; for 0.166667h;
DOI:10.1021/jo00299a030

Reference yield:

: 58763-00-1,828937-29-7
((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 127646-32-6
(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / CrO₃, pyridine / CH₂Cl₂ / 0.33 h / 25 °C

2: 1) t-BuOK, 2) MsCl, (i-Pr₂)EtN / 1) THF/t-BuOH, 0 to 25 deg C, 12 h at 25 deg C, 2) CH₂Cl₂, -78 to -30 deg C, 30 min at -30 deg C

3: 1) potassium trimethylsilanoate, 2) ozone / 1) DMF, 0 deg C, 30 min, 2) methanol, -78 deg C

4: 94 percent / pyridine / CH₂Cl₂ / 0.17 h

With pyridine; chromium(VI) oxide; potassium tert-butylate; potassium trimethylsilonate; ozone; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo00299a030

Reference yield:

: 32445-75-3
D-Ribose

: 127646-32-6
(S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / conc. HCl / 18 h / Heating

2: 71 percent / CrO₃, pyridine / CH₂Cl₂ / 0.33 h / 25 °C

3: 1) t-BuOK, 2) MsCl, (i-Pr₂)EtN / 1) THF/t-BuOH, 0 to 25 deg C, 12 h at 25 deg C, 2) CH₂Cl₂, -78 to -30 deg C, 30 min at -30 deg C

4: 1) potassium trimethylsilanoate, 2) ozone / 1) DMF, 0 deg C, 30 min, 2) methanol, -78 deg C

5: 94 percent / pyridine / CH₂Cl₂ / 0.17 h

With pyridine; chromium(VI) oxide; hydrogenchloride; potassium tert-butylate; potassium trimethylsilonate; ozone; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo00299a030