Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester
• CAS No.: 127000-08-2
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252

Synonyms:Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

There total 5 articles about Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl 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: 78.0%

benzoyl chloride (98-88-4) + L-rhamnal (53657-42-4) → 1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol (34820-21-8) + 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol (104006-65-7) + 4-O-benzoyl-L-rhamnal (91861-12-0,104069-01-4,127000-08-2,130061-17-5)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/j.carres.2018.10.014

Reference yield: 78.0%

benzoyl chloride (98-88-4) + L-fucal (80483-16-5) → Benzoic acid (2S,3S,4S)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (91861-12-0,104069-01-4,127000-08-2,130061-17-5) + 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-lyxo-hex-1-enitol (130061-11-9) + dibenzoyl fucal (130061-16-4)

Guidance literature:

With triethylamine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/ja00180a037

Reference yield: 72.0%

Benzoic acid (2R,3S,4R)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (126900-82-1) → Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (127000-08-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2.5h;

upstream raw materials:

Benzoic acid (2R,3S,4R)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

benzoyl chloride

L-fucal

3,4-di-O-acetyl-L-fucal

Downstream raw materials:

3-Chloro-benzoic acid (2R,3S,4R,5R,6R)-5-benzoyloxy-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yl ester

2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

3-Chloro-benzoic acid (2S,3R,6R)-2-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl ester

Imidazole-1-carbothioic acid O-[(2S,3R,6R)-2-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl] ester

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