2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

Chemical Name:2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
CAS No.:307980-34-3
Molecular Formula:C₁₈H₂₃BrO₆
Molecular Weight:415.281
Hs Code.:

Synonyms:2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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Chemical Property of 2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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Technology Process of 2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 3 articles about 2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl 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: 98.0%

: 23202-83-7,2592-42-9
5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 598-72-1,10327-08-9
2-Bromopropionic acid

: 307980-34-3
2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: 2-Bromopropionic acid; With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.5h;

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose; With dmap; In dichloromethane; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1021/ol006449e

Reference yield:

: 100-39-0
benzyl bromide

: 307980-34-3
2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.17 h / -78 °C

1.2: 61 percent / tetrabutylammonium iodide / tetrahydrofuran / 2.5 h / 20 °C

2.1: DCC / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 98 percent / 4-DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol006449e

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 307980-34-3
2-Bromo-propionic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 0.17 h / -78 °C

1.2: 61 percent / tetrabutylammonium iodide / tetrahydrofuran / 2.5 h / 20 °C

2.1: DCC / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 98 percent / 4-DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol006449e