Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

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Chemical Name:Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester
CAS No.:786709-76-0
Molecular Formula:C₂₉H₃₁FO₆
Molecular Weight:494.56
Hs Code.:

Synonyms:Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

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Chemical Property of Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

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Technology Process of Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

There total 9 articles about Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl 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: 71.0%

: 504-63-2
trimethyleneglycol

: 786709-74-8
1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose

: 786709-76-0
Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: With toluene-4-sulfonic acid; In benzene; Heating;
DOI:10.1021/ol048459b

Reference yield:

: 19139-80-1,34370-91-7,68354-70-1,70798-12-8,59358-33-7
((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 786709-76-0
Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂ / 0.5 h

2: 1.36 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 °C

3: sulfuric acid / 2 h / Heating

4: 1.28 g / NaH / dimethylformamide / 20 °C

5: 88 percent / hydrochloric acid / dioxane / Heating

6: 92 percent / NaBH₄ / methanol / 2 h / 20 °C

7: 83 percent / pyridine / CHCl₃ / 16 h / 20 °C

8: 59 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

9: 71 percent / p-toluenesulfonic acid monohydrate / benzene / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene; 8: Swern oxidation;
DOI:10.1021/ol048459b

Reference yield:

: 895558-57-3
((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate

: 786709-76-0
Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.36 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 °C

2: sulfuric acid / 2 h / Heating

3: 1.28 g / NaH / dimethylformamide / 20 °C

4: 88 percent / hydrochloric acid / dioxane / Heating

5: 92 percent / NaBH₄ / methanol / 2 h / 20 °C

6: 83 percent / pyridine / CHCl₃ / 16 h / 20 °C

7: 59 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

8: 71 percent / p-toluenesulfonic acid monohydrate / benzene / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene; 7: Swern oxidation;
DOI:10.1021/ol048459b