(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:175978-38-8
Molecular Formula:C₃₁H₃₆O₁₀
Molecular Weight:568.621
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 10 articles about (2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl 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:

: 175978-37-7
(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid

: 74-88-4
methyl iodide

: 175978-38-8
(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃; Yield given;
DOI:10.1016/0008-6215(95)00346-0

Reference yield:

: 40608-06-8
levulinic anhydride

: 175978-38-8
(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 1 h

2: CrO₃, 3.5M aq. H₂SO₄ / acetone / 0 °C

3: KHCO₃ / dimethylformamide / 0 °C

With chromium(VI) oxide; sulfuric acid; potassium hydrogencarbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(95)00346-0

Reference yield:

: 98-88-4
benzoyl chloride

: 175978-38-8
(2R,3S,4S,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

2: 80percent aq. AcOH / 0.25 h / 100 °C

3: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h

5: CrO₃, 3.5M aq. H₂SO₄ / acetone / 0 °C

6: KHCO₃ / dimethylformamide / 0 °C

With chromium(VI) oxide; dmap; sulfuric acid; potassium hydrogencarbonate; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(95)00346-0