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

Base Information

• Chemical Name: (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone
• CAS No.: 748154-81-6
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• Mol file: 748154-81-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone 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: 35.0%

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one (226885-92-3) → (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (748154-81-6)

Guidance literature:

With acetic acid; In methanol; at 0 ℃;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

D-glucose (50-99-7) → (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (748154-81-6)

Guidance literature:

Multi-step reaction with 14 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

With 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:

methyl-alpha-D-glucopyranoside (97-30-3) → (4S,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (748154-81-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 87 percent / TsOH / dimethylformamide / 45 °C

2: 66 percent / NaH / dimethylformamide

3: 100 percent / NaH / dimethylformamide

4: 80 percent / LiAlH₄ / tetrahydrofuran / 50 °C

5: 100 percent / NaH / dimethylformamide / 20 °C

6: 80 percent / AcOH; H₂O / 70 °C

7: 100 percent / I₂; Ph₃P; Imid_. / toluene

8: 91 percent / DIPEA / CH₂Cl₂

9: 100 percent / t-BuOK / tetrahydrofuran

10: Hg(OCOCF₃)2 / acetone; H₂O

11: MsCl; Et₃N / CH₂Cl₂

12: 44 percent / DBU / toluene

13: 35 percent / AcOH / methanol / 0 °C

With 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; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 10: Ferrier cyclization;

DOI:10.1016/j.tetlet.2004.05.129

upstream raw materials:

(4S,6R)-4-<(4-methoxybenzyl)oxy>-6-<(methoxymethyl)oxy>-2-cyclohexene-1-one

D-glucose

methyl-alpha-D-glucopyranoside

methyl 3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside

Downstream raw materials:

(diethoxy-phosphoryl)-acetic acid 5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester

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

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

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