(2R)-2-bromo-3-dehydroquinic acid

Base Information

• Chemical Name: (2R)-2-bromo-3-dehydroquinic acid
• CAS No.: 189366-39-0
• Molecular Formula: C₇H₉BrO₆
• Molecular Weight: 269.049
• Mol file: 189366-39-0.mol

Synonyms:(2R)-2-bromo-3-dehydroquinic acid

Chemical Property of (2R)-2-bromo-3-dehydroquinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-bromo-3-dehydroquinic acid

There total 5 articles about (2R)-2-bromo-3-dehydroquinic acid 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: 95.0%

(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-6-oxa-bicyclo[3.2.1]octane-3,7-dione (189366-38-9) → (2R)-2-bromo-3-dehydroquinic acid (189366-39-0)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 40 ℃; for 72h;

DOI:10.1039/a606104d

Reference yield:

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one (216662-57-6) → (2R)-2-bromo-3-dehydroquinic acid (189366-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / H₂ / 10percent Pd/C / acetic acid / 48 h / Ambient temperature

2: 54 percent / DMAP, Et₃N, Bu₄NI / dimethylformamide / 24 h / 90 °C

3: 87 percent / PDC, MS 4A / CH₂Cl₂ / 2 h / Ambient temperature

4: 89 percent / Br₂*dioxane / diethyl ether / 2 h / Ambient temperature

5: 95 percent / aq. AcOH / tetrahydrofuran / 72 h / 40 °C

With dmap; dipyridinium dichromate; hydrogen; dioxane dibromide; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1039/a606104d

Reference yield:

(1R,3R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one (164029-69-0) → (2R)-2-bromo-3-dehydroquinic acid (189366-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / PDC, MS 4A / CH₂Cl₂ / 2 h / Ambient temperature

2: 89 percent / Br₂*dioxane / diethyl ether / 2 h / Ambient temperature

3: 95 percent / aq. AcOH / tetrahydrofuran / 72 h / 40 °C

With dipyridinium dichromate; dioxane dibromide; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/a606104d

upstream raw materials:

(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-6-oxa-bicyclo[3.2.1]octane-3,7-dione

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one

(1R,3R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one

(1R,3R,4S)-4-(tert-butyldimethylsiloxy)-1-hydroxy-5-oxocyclohexane-1,3-carbolactone

Downstream raw materials:

2-bromo-3-dehydroshikimic acid

Refernces