(2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate
• CAS No.: 1192757-03-1
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 1192757-03-1.mol

Synonyms:(2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate

Chemical Property of (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate

There total 7 articles about (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate 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: 89.0%

vinyl acetate (108-05-4,9003-20-7) + ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-82-3) → (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate (1192757-03-1)

Guidance literature:

With Rhizomucor miehei lipase; In di-isopropyl ether; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol902107g

Reference yield:

((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-82-3) + acetic anhydride (108-24-7) → (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate (1192757-03-1) + (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2Hpyran-4-yl benzoate

Guidance literature:

With C₄₅H₃₆FeN₂; N-ethyl-N,N-diisopropylamine; In tert-Amyl alcohol; at -2 - 20 ℃; for 16h; Overall yield = 34 %; Overall yield = 22 mg; enantioselective reaction;

DOI:10.1002/anie.201308268

Reference yield:

C16H18O5 → (2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate (1192757-03-1) + (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2Hpyran-4-yl benzoate

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; water / tetrahydrofuran / 0 - 20 °C

2: C₄₅H₃₆FeN₂; N-ethyl-N,N-diisopropylamine / tert-Amyl alcohol / 16 h / -2 - 20 °C

With sodium tetrahydroborate; C₄₅H₃₆FeN₂; water; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tert-Amyl alcohol;

DOI:10.1002/anie.201308268

upstream raw materials:

vinyl acetate

((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

acetic anhydride

(1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one