4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester
CAS No.:866476-72-4
Molecular Formula:C₁₇H₂₂O₇
Molecular Weight:338.357
Hs Code.:

Synonyms:4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

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Chemical Property of 4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

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Technology Process of 4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

There total 5 articles about 4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-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: 93.0%

: 866476-71-3
benzyl 2-O-levulinyl-3,4-O-isopropylidene-β-L-arabinopyranoside

: 866476-72-4
4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: In water; acetic acid; at 70 ℃; for 1h;
DOI:10.1016/j.carres.2005.06.024

Reference yield:

: 5328-37-0
L-arabinose

: 866476-72-4
4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / BF₃*Et₂O / 2.5 h / 90 - 100 °C

2: 79 percent / p-TsOH*H₂O / dimethylformamide / 12 h / 20 °C

3: 100 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 93 percent / acetic acid; H₂O / 1 h / 70 °C

With dmap; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2005.06.024

Reference yield:

: 7473-38-3
benzyl β-L-arabinopyranoside

: 866476-72-4
4-Oxo-pentanoic acid (2S,3R,4S,5S)-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 79 percent / p-TsOH*H₂O / dimethylformamide / 12 h / 20 °C

2: 100 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

3: 93 percent / acetic acid; H₂O / 1 h / 70 °C

With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2005.06.024