Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester

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Chemical Name:Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester
CAS No.:786710-14-3
Molecular Formula:C₂₂H₂₅FO₅
Molecular Weight:388.436
Hs Code.:

Synonyms:Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester

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

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

There total 9 articles about Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[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: 87.0%

: 504-63-2
trimethyleneglycol

: 786710-13-2
3-O-benzyl-1,4-dideoxy-4-fluoro-5-O-benzoyl-D-xylulose

: 786710-14-3
Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 18h; Heating;
DOI:10.1021/ol048459b

Reference yield:

: (3R,4S,5R)-4-Benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-ol

: 786710-14-3
Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 18 percent / pyridine / 2 h

2: 96 percent / sodium methoxide / methanol / 0.25 h / 20 °C

3: pyridine / CH₂Cl₂ / 1 h / 4 °C

4: 0.80 g / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 4 °C

5: 82 percent / hydrochloric acid / dioxane / 48 h / Heating

6: 70 percent / NaBH₄ / methanol / 1.5 h / 20 °C

7: 87 percent / pyridine / 20 °C

8: 79 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

9: 87 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating

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

Reference yield:

: 786710-09-6
methyl 2,5-dideoxy-2-fluoro-3-O-benzyl-α-D-arabinofuranoside

: 786710-14-3
Benzoic acid (2R,3R)-3-benzyloxy-2-fluoro-3-(2-methyl-[1,3]dioxan-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / hydrochloric acid / dioxane / 48 h / Heating

2: 70 percent / NaBH₄ / methanol / 1.5 h / 20 °C

3: 87 percent / pyridine / 20 °C

4: 79 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

5: 87 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; benzene; 4: Swern oxidation;
DOI:10.1021/ol048459b