(2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Base Information

• Chemical Name: (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate
• CAS No.: 110418-97-8
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 110418-97-8.mol

Synonyms:(2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Chemical Property of (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

There total 11 articles about (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-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: 70.0%

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (83497-33-0) → (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (110418-97-8)

Guidance literature:

With hydrogen; triethylamine; In ethanol; Inert atmosphere;

DOI:10.1002/cjoc.201201084

Reference yield:

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (83497-33-0) → methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside (104652-05-3) + (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (110418-97-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 60 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00278a035

Reference yield:

Benzoic acid (2R,3R,4S,6S)-6-methoxy-2-methyl-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (203498-97-9) → (2R,3S,4S,6S)-4-hydroxy-6-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (110418-97-8)

Guidance literature:

With hydrogenchloride; In methanol; at 23 ℃; for 0.25h;

DOI:10.1080/07328309808005770

upstream raw materials:

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

Benzoic acid (2R,3R,4R,6S)-6-methoxy-2-methyl-4-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3R,4S,6S)-6-methoxy-2-methyl-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-6-methoxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

methyl 4-O-benzoyl-2,3,6-trideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-α-D-ribo-hexopyranoside

methyl 4-O-benzoyl-2,3,6-trideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-α-D-arabino-hexopyranoside

methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Benzoic acid (2R,3S,6S)-4-[(E)-hydroxyimino]-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester