[(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid

Base Information

• Chemical Name: [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid
• CAS No.: 870180-43-1
• Molecular Formula: C₁₉H₁₈F₃N₇O₅S
• Molecular Weight: 513.457
• Mol file: 870180-43-1.mol

Synonyms:[(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid

Chemical Property of [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid

There total 5 articles about [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic 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: 25.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (1S,2R,3R,4S,6R)-4,6-Diazido-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexane-1,2-diol (609342-87-2) → [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid (870180-43-1) + [(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid (870180-47-5)

Guidance literature:

(1S,2R,3R,4S,6R)-4,6-Diazido-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexane-1,2-diol; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2005.08.027

Reference yield:

4-mercapto 7-trifluoromethyl quinoline (64415-07-2) → [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid (870180-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / acetonitrile / 0.25 h / 20 °C

1.2: 1.15 g / acetonitrile / 2.5 h / 20 °C

2.1: 91 percent / aq. NH₃ / methanol / 16 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 20 percent / tetrahydrofuran / 16 h / 20 °C

With ammonium hydroxide; sodium hydride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.bmcl.2005.08.027

Reference yield:

[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate (236115-61-0) → [(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid (870180-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / AcOH; Ac₂O / 60 h / 20 °C

2.1: SO₂Cl₂ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: NaH / acetonitrile / 0.25 h / 20 °C

3.2: 1.15 g / acetonitrile / 2.5 h / 20 °C

4.1: 91 percent / aq. NH₃ / methanol / 16 h / 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 20 percent / tetrahydrofuran / 16 h / 20 °C

With ammonium hydroxide; sulfuryl dichloride; acetic anhydride; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Pummerer rearrangement;

DOI:10.1016/j.bmcl.2005.08.027

upstream raw materials:

bromoacetic acid tert-butyl ester

(1S,2R,3R,4S,6R)-4,6-Diazido-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexane-1,2-diol

4-mercapto 7-trifluoromethyl quinoline

[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

Downstream raw materials:

(3-{2-[(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-ethylamino}-propyl)-carbamic acid tert-butyl ester

(3-{2-[(1S,2R,3R,4S,6R)-4,6-Diamino-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-ethylamino}-propyl)-carbamic acid tert-butyl ester

2-[(1S,2R,3R,4S,6R)-4,6-Diazido-2-hydroxy-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide