Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Base Information

• Chemical Name: Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester
• CAS No.: 748154-82-7
• Molecular Formula: C₁₆H₁₇BrO₅
• Molecular Weight: 369.212
• Mol file: 748154-82-7.mol

Synonyms:Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Chemical Property of Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

There total 13 articles about Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl 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: 68.0%

2-bromoacetyl chloride (22118-09-8) + (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (748154-81-6) → Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-82-7)

Guidance literature:

With pyridine; In dichloromethane; at -78 ℃;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

D-glucose (50-99-7) → Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-82-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 56 percent / AcCl / Heating

2: 87 percent / TsOH / dimethylformamide / 45 °C

3: 66 percent / NaH / dimethylformamide

4: 100 percent / NaH / dimethylformamide

5: 80 percent / LiAlH₄ / tetrahydrofuran / 50 °C

6: 100 percent / NaH / dimethylformamide / 20 °C

7: 80 percent / AcOH; H₂O / 70 °C

8: 100 percent / I₂; Ph₃P; Imid_. / toluene

9: 91 percent / DIPEA / CH₂Cl₂

10: 100 percent / t-BuOK / tetrahydrofuran

11: Hg(OCOCF₃)2 / acetone; H₂O

12: MsCl; Et₃N / CH₂Cl₂

13: 44 percent / DBU / toluene

14: 35 percent / AcOH / methanol / 0 °C

15: 68 percent / pyr. / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; potassium tert-butylate; water; iodine; mercury(II) trifluoroacetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 11: Ferrier cyclization;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-92-3) → Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester (748154-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / AcOH / methanol / 0 °C

2: 68 percent / pyr. / CH₂Cl₂ / -78 °C

With pyridine; acetic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.05.129

upstream raw materials:

2-bromoacetyl chloride

(4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

D-glucose

methyl-alpha-D-glucopyranoside

Downstream raw materials:

(6S,7aR)-6-hydroxy-7,7a-dihydrobenzofuran-2(6H)-one

6-(4-methoxy-benzyloxy)-7,7a-dihydro-6H-benzofuran-2-one