(2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene

Base Information

• Chemical Name: (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene
• CAS No.: 171013-12-0
• Molecular Formula: C₃₂H₃₅BrO₇
• Molecular Weight: 611.53
• Mol file: 171013-12-0.mol

Synonyms:(2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene

Chemical Property of (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene

There total 8 articles about (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene 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:

methyl 3′-hydroxy-2′-methoxybenzoate (2169-25-7) → (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene (171013-12-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / CH₂Cl₂ / 1 h / 0 °C

2: 2.) K₂HPO₃-deactivated silica gel / 1.) 0 deg C, 2 d, 2.) EtOAc, 1 h

3: 47 percent / K₂CO₃, n-Bu₄NI / dimethylsulfoxide / 72 h / 28 °C

4: 95 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

5: 81 percent / MnO₂ / diethyl ether / 1 h / 23 °C

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

7: 47 percent / tetrahydrofuran / 18 h / Heating

8: 67 percent / (n-Bu)3SnH / toluene / 0.5 h

9: 66 percent / N-bromosuccinimide / tetrahydrofuran / 1 h / -78 °C

With manganese(IV) oxide; N-Bromosuccinimide; n-butyllithium; K₂HPO₃-deactivated silica gel; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/ja00149a012

Reference yield:

benzyl bromide (100-39-0) → (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene (171013-12-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 47 percent / K₂CO₃, n-Bu₄NI / dimethylsulfoxide / 72 h / 28 °C

2: 95 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

3: 81 percent / MnO₂ / diethyl ether / 1 h / 23 °C

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

5: 47 percent / tetrahydrofuran / 18 h / Heating

6: 67 percent / (n-Bu)3SnH / toluene / 0.5 h

7: 66 percent / N-bromosuccinimide / tetrahydrofuran / 1 h / -78 °C

With manganese(IV) oxide; N-Bromosuccinimide; n-butyllithium; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; toluene;

DOI:10.1021/ja00149a012

Reference yield:

methyl 6-acetoxy-6-methoxy-1-oxo-2,4-cyclohexadiene-5-carboxylate (132019-87-5) → (2'R)-1-benzoxy-3-<2-(benzoxymethoxy)-1-propyl>-5-bromo-2,6-dimethoxy-4-(methoxymethoxy)naphthalene (171013-12-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.) K₂HPO₃-deactivated silica gel / 1.) 0 deg C, 2 d, 2.) EtOAc, 1 h

2: 47 percent / K₂CO₃, n-Bu₄NI / dimethylsulfoxide / 72 h / 28 °C

3: 95 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

4: 81 percent / MnO₂ / diethyl ether / 1 h / 23 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

6: 47 percent / tetrahydrofuran / 18 h / Heating

7: 67 percent / (n-Bu)3SnH / toluene / 0.5 h

8: 66 percent / N-bromosuccinimide / tetrahydrofuran / 1 h / -78 °C

With manganese(IV) oxide; N-Bromosuccinimide; n-butyllithium; K₂HPO₃-deactivated silica gel; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; toluene;

DOI:10.1021/ja00149a012

upstream raw materials:

methyl 3′-hydroxy-2′-methoxybenzoate

benzyl bromide

methyl 6-acetoxy-6-methoxy-1-oxo-2,4-cyclohexadiene-5-carboxylate

methyl 2,6-dimethoxy-1-hydroxy-8-(methoxymethoxy)naphthalene-3-carboxylate