Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester
• CAS No.: 592517-66-3
• Molecular Formula: C₂₀H₂₁F₃O₈S
• Molecular Weight: 478.443

Synonyms:Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester

Chemical Property of Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester

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Technology Process of Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester

There total 4 articles about Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-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: 45.0%

trifluoroacetic anhydride (407-25-0) + 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (S)-oxide (592517-58-3) → Benzoic acid (3aR,7S,7aR)-7-acetoxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-(6E)-ylidenemethyl ester + benzoic acid 7-acetoxy-2,2-dimethyl-3a,7a-dihydro-4H-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-6-hydroxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester (592517-66-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(03)00842-6

Reference yield: 40.0%

trifluoroacetic anhydride (407-25-0) + 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (R)-oxide (592517-54-9) → Benzoic acid (3aR,7S,7aR)-7-acetoxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-(6E)-ylidenemethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-6-hydroxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester (592517-66-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2004.06.006

Reference yield: 40.0%

trifluoroacetic anhydride (407-25-0) + 4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (R)-oxide (592517-54-9) → Benzoic acid (3aR,7S,7aR)-7-acetoxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-(6E)-ylidenemethyl ester + benzoic acid 7-acetoxy-2,2-dimethyl-3a,7a-dihydro-4H-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-6-hydroxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester + Benzoic acid (3aR,6R,7S,7aR)-7-acetoxy-2,2-dimethyl-6-(2,2,2-trifluoro-acetoxy)-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-6-ylmethyl ester (592517-66-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(03)00842-6

upstream raw materials:

trifluoroacetic anhydride

4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (R)-oxide

4-acetoxy-6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose (S)-oxide

6-O-benzoyl-1,5-dideoxy-2,3-O-isopropylidene-5-thio-D-glucopyranose

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