methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate

Base Information

• Chemical Name: methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate
• CAS No.: 84751-48-4
• Molecular Formula: C₂₈H₃₆O₈
• Molecular Weight: 500.589
• Mol file: 84751-48-4.mol

Synonyms:methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate

Chemical Property of methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate

There total 7 articles about methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate 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: 93.0%

methyl (1S,4R,4aR,7S,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-hydroxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate (84751-47-3) + benzoic acid (65-85-0,8013-63-6) → methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate (84751-48-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 0.25h;

DOI:10.1021/ja00343a072

Reference yield:

ethyl (1SR,2RS,3RS,4RS)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate (84751-41-7,89299-58-1,89299-59-2) → methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate (84751-48-4)

Guidance literature:

Multi-step reaction with 7 steps

1: KOOCNNCOOK / methanol; acetic acid / 8 h / 0 °C

2: aq. KOH / tetrahydrofuran / 0 °C

3: 1.) D(-)-α-phenylglycinol, dicyclohexylcarbodiimide, 2.) aq. HCl / 1.) CH3CN, 2.) 65 deg C, 3 h

4: 75 percent / DBU / CH₂Cl₂ / 2 h / Heating

5: 70 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 14 h / 125 °C

6: 1.) MCPBA, 2.) trimethylphosphite / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, reflux, 2.5 h

7: 93 percent / DEAD, Ph₃P / tetrahydrofuran / 0.25 h

With hydrogenchloride; potassium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; (2S)-2-phenylglycinol; potassium diazodicarboxylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; acetic acid; toluene;

DOI:10.1021/ja00343a072

Reference yield:

Ethyl 2-exo,3-endo-3-Nitro-7-oxabicyclo<2.2.1>heptane-2-carboxylate (89299-57-0) → methyl (1S,4R,4aR,7R,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-benzoxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate (84751-48-4)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. KOH / tetrahydrofuran / 0 °C

2: 1.) D(-)-α-phenylglycinol, dicyclohexylcarbodiimide, 2.) aq. HCl / 1.) CH3CN, 2.) 65 deg C, 3 h

3: 75 percent / DBU / CH₂Cl₂ / 2 h / Heating

4: 70 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 14 h / 125 °C

5: 1.) MCPBA, 2.) trimethylphosphite / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, reflux, 2.5 h

6: 93 percent / DEAD, Ph₃P / tetrahydrofuran / 0.25 h

With hydrogenchloride; potassium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; (2S)-2-phenylglycinol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; phosphorous acid trimethyl ester; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00343a072

upstream raw materials:

methyl (1S,4R,4aR,7S,8R,8aR)-1,3,4,7,8,8a-hexahydro-7-hydroxy-8-<2-((2R,4R,6S)-tetrahydro-4,6-dimethoxy-2H-pyran-2-yl)-ethyl>-1,4-epoxynaphthalene-4a(2H)-carboxylate

benzoic acid

2-exo,3-endo-3-Nitro-7-oxabicyclo<2.2.1>heptane-2-carboxylic Acid

ethyl (1SR,2RS,3RS,4RS)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

Downstream raw materials:

mevastatin

Refernces

• 1、 Grieco, Paul A.,Zelle, Robert E.,Lis, Randall,Finn, John. "Total Synthesis of the Hypochloesterolemic Agent (+)-Compactin". . p. 1403 - 1404. Retrieved 2007/10/02.