(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:200346-52-7
Molecular Formula:C₁₉H₂₅BrO₆
Molecular Weight:429.308
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

There total 1 articles about (3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 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: 80.0%

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 3433-80-5
1-Bromo-2-bromomethyl-benzene

: 200346-52-7
(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 0 - 20 ℃;

1-Bromo-2-bromomethyl-benzene; In dichloromethane; at 20 ℃;
DOI:10.1002/adsc.201100988

Reference yield:

: 200346-52-7
(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: (3aR,5S,6S,6aR)-6-(2-Bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: AcOH / H₂O / 12 h / 20 °C

2: sodium periodate / methanol; H₂O / 0 °C

With sodium periodate; acetic acid; In methanol; water;
DOI:10.1016/j.tet.2006.09.080

Reference yield:

: 200346-52-7
(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 1030614-06-2
(3aR,5R,6S,6aR)-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol

Guidance literature:: Multi-step reaction with 3 steps

1: acetic acid / H₂O / 12 h / 20 °C

2: NaIO₄ / methanol; H₂O / 0 °C

3: NaBH₄ / ethanol / 2 h / 0 - 20 °C

With sodium tetrahydroborate; sodium periodate; acetic acid; In methanol; ethanol; water;
DOI:10.1016/j.tet.2005.07.054