2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester
CAS No.:1029039-49-3
Molecular Formula:C₁₈H₂₀O₆S
Molecular Weight:364.419
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

There total 20 articles about 2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl 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:

: 100-39-0
benzyl bromide

: 1029039-49-3
2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: naH / dimethylformamide / 3 h / 20 °C

2: TBAF / dimethylformamide / 4 h / 20 °C

3: 70 percent / CH₂Cl₂ / 8 h / 20 °C

4: 72 percent / Bu₄NHSO₄ / acetonitrile; H₂O / 15 h / 65 °C

5: 97 percent / Ag₂CO₃/Celite / benzene / 2.5 h / Heating

6: 87 percent / DMSO; TFAA; Et₃N / -60 - 20 °C

7: 95 percent / CHCl₃ / 20 °C

8: pyridine / CHCl₃

With pyridine; Celite; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride; In dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1: Substitution / 2: Substitution / 3: Acylation / 4: Addition / 5: Oxidation / 6: Oxidation / 7: Substitution / 8: Elimination;
DOI:10.1021/ol991176c

Reference yield:

: 3282-30-2
pivaloyl chloride

: 1029039-49-3
2,2-Dimethyl-propionic acid (2R,3S)-3-benzyloxy-4,6-dioxo-5-thioxo-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / CH₂Cl₂ / 8 h / 20 °C

2: 69 percent / HCl / tetrahydrofuran; H₂O / 6 h / 40 °C

3: 74 percent / Ag₂CO₃/Celite / benzene / 3 h / 80 °C

4: 86 percent / DMSO; TFAA; Et₃N / -60 - 20 °C

5: 95 percent / CHCl₃ / 20 °C

6: pyridine / CHCl₃

7: pyridine / CHCl₃

With pyridine; hydrogenchloride; Celite; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; chloroform; water; benzene; 1: Acylation / 2: Addition / 3: Oxidation / 4: Oxidation / 5: Substitution / 6: Elimination / 7: Elimination;
DOI:10.1021/ol991176c