methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate

Base Information

• Chemical Name: methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate
• CAS No.: 184886-39-3
• Molecular Formula: C₁₄H₂₄O₈
• Molecular Weight: 320.34
• Mol file: 184886-39-3.mol

Synonyms:methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate

Chemical Property of methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate

There total 17 articles about methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate 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: 95.0%

methyl shikimate (40983-58-2) + chloromethyl methyl ether (107-30-2) → methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate (184886-39-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1002/ejoc.200800830

Reference yield:

C13H19BrO5 (146830-40-2) → methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate (184886-39-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / iPr₂EtN / CH₂Cl₂

2: 79 percent / Zn, AcOH / ethanol

3: 86 percent / NaHCO₃ / diphenyl ether / 0.5 h / 260 °C

4: Et₃N, DMAP / CH₂Cl₂ / 0 °C

5: Bu₃SnH, AIBN / benzene / 80 °C

6: 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / Heating

7: 100 percent / imidazole / dimethylformamide

8: iPrEtN, DMAP / CH₂Cl₂

9: TBAF / tetrahydrofuran

10: SO₃*Py, Et₃N / dimethylsulfoxide

11: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

12: CH₂Cl₂

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1996.987

Reference yield:

C13H17BrO3 (146830-39-9) → methyl (3R,4S,5R)-3,4,5-tris(methoxymethoxy)cyclohex-1-enecarboxylate (184886-39-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 86 percent / OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O

2: 97 percent / iPr₂EtN / CH₂Cl₂

3: 79 percent / Zn, AcOH / ethanol

4: 86 percent / NaHCO₃ / diphenyl ether / 0.5 h / 260 °C

5: Et₃N, DMAP / CH₂Cl₂ / 0 °C

6: Bu₃SnH, AIBN / benzene / 80 °C

7: 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / Heating

8: 100 percent / imidazole / dimethylformamide

9: iPrEtN, DMAP / CH₂Cl₂

10: TBAF / tetrahydrofuran

11: SO₃*Py, Et₃N / dimethylsulfoxide

12: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

13: CH₂Cl₂

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1996.987

upstream raw materials:

diazomethane

C₁₃H₁₉BrO₅

C₁₃H₁₇BrO₃

Acetic acid (1S,4R,4aS,5R,8S,8aR)-8-methoxymethoxy-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-yl ester

Downstream raw materials:

methyl shikimate

shikimic acid

methyl (1S,2R,3R,4S,5R)-1,2-dihyroxy-3,4,5-tris(methoxymethoxy)cyclohexanecarboxylate