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

Base Information

Chemical Name:(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:175978-45-7
Molecular Formula:C₃₂H₃₂O₉S
Molecular Weight:592.667
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about (2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-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:

: 175978-44-6
(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid

: 74-88-4
methyl iodide

: 175978-45-7
(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-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

: 175978-45-7
(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 1 h

2: Dowex 50 (H⁺) / methanol / Ambient temperature

3: pyridinium dichromate / dimethylformamide

4: KHCO₃ / dimethylformamide / 0 °C

With dipyridinium dichromate; Dowex 50 (H⁺); potassium hydrogencarbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00346-0

Reference yield:

: 108-98-5
thiophenol

: 175978-45-7
(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 25 °C

2: MeONa / methanol

3: TFA / 3 h / Ambient temperature

4: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

5: 80percent aq. AcOH / 0.25 h / 100 °C

6: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

7: Et₃N / CH₂Cl₂ / 1 h

8: Dowex 50 (H⁺) / methanol / Ambient temperature

9: pyridinium dichromate / dimethylformamide

10: KHCO₃ / dimethylformamide / 0 °C

With dmap; dipyridinium dichromate; Dowex 50 (H⁺); boron trifluoride diethyl etherate; sodium methylate; potassium hydrogencarbonate; acetic acid; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00346-0