Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

Base Information

• Chemical Name: Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester
• CAS No.: 130481-52-6
• Molecular Formula: C₁₇H₂₂O₉S
• Molecular Weight: 402.422

Synonyms:Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

Chemical Property of Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

Chemical Property:

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Technology Process of Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

There total 2 articles about Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-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: 68.0%

1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-allofuranose (64993-88-0) + benzoyl chloride (98-88-4) → Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (130481-52-6)

Guidance literature:

With pyridine; for 16h; -30 deg C --> 25 deg C;

DOI:10.1016/S0040-4039(00)94484-8

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose (14728-80-4) → Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (130481-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 80percent aq. AcOH / 25 °C

2: 68 percent / pyridine / 16 h / -30 deg C --> 25 deg C

With pyridine; acetic acid;

DOI:10.1016/S0040-4039(00)94484-8

Reference yield: 85.0%

Benzoic acid (R)-2-hydroxy-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester (130481-52-6) + benzoic acid (65-85-0,8013-63-6) → C24H26O10S (141980-88-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate;

DOI:10.1021/jm00094a014

upstream raw materials:

1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-allofuranose

benzoyl chloride

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose

Downstream raw materials:

Benzoic acid (R)-2-((3aR,5R,6R,6aR)-6-methanesulfonyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-p-tolyloxythiocarbonyloxy-ethyl ester

C₂₄H₂₆O₁₀S

1-(3'-azido-2',3'-dideoxy-α-L-talofuranosyl)thymine

2,3'-anhydro-1-(5',6'-di-O-benzoyl-2'-deoxy-α-L-idofuranosyl)thymine

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