methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate

Base Information

• Chemical Name: methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate
• CAS No.: 404936-50-1
• Molecular Formula: C₂₇H₃₆O₆
• Molecular Weight: 456.579
• Mol file: 404936-50-1.mol

Synonyms:methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate

Chemical Property of methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate

There total 19 articles about methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate 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: 99.0%

methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-6,8-O-isopropylidene-1-undecenyl]-6-methoxybenzoate (404936-49-8) → methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate (404936-50-1)

Guidance literature:

With acetic acid; at 20 ℃; for 1.33333h;

DOI:10.1021/ol017261d

Reference yield:

methyl 2-methoxy-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate (145645-18-7) → methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate (404936-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / P(2-furyl)3; NMP; LiCl / [Pd₂(dba)3]

With 1-methyl-pyrrolidin-2-one; trifuran-2-yl-phosphane; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;

Reference yield:

5-oxo-tetrahydro-furan-2-carboxylic acid (4344-84-7,21461-84-7,53558-93-3,83829-70-3) → methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoate (404936-50-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 70 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating

2.1: 91 percent / (+/-)-camphersulfonic acid / acetone / 3 h / 35 °C

3.1: NaH / tetrahydrofuran / 0.75 h

3.2: 84 percent / tetrahydrofuran / 16 h

4.1: 93 percent / AcOH / 3 h / 20 °C

5.1: CH₃C(OCH₃)3; PPTS / CH₂Cl₂ / 3 h / 20 °C

5.2: AcBr / CH₂Cl₂ / 0.75 h

5.3: 99 percent / K₂CO₃ / methanol / 2 h

6.1: t-BuLi; TMEDA / tetrahydrofuran; pentane / 3 h / -20 °C

6.2: 89 percent / tetrahydrofuran; pentane / 2 h / -20 °C

7.1: 90 percent / Hg(ClO₄)2*4H₂O; iPr₂NH / tetrahydrofuran / 1 h

8.1: (EtO)2BMe / tetrahydrofuran; methanol / 0.5 h / -78 °C

8.2: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 3 h / -78 °C

9.1: 97 percent / (+/-)-camphersulfonic acid / 1 h / 20 °C

10.1: 93 percent / iPr₂NH / CH₂Cl₂ / 0.42 h / 20 °C

11.1: 92 percent / NaI / acetone / 48 h

12.1: 77 percent / H₂NCH₂CH₂NH₂ / dimethylsulfoxide / 96 h / 20 °C

13.1: Bu₃SnH; AIBN / toluene / 16 h / Heating

13.2: 310.0 mg / tri-2-furyl-phosphine; LiCl; N-methylpyrrolidine / tris-(dibenzylidenacetone)-dipalladium / 16 h / 60 °C

14.1: 99 percent / aq. AcOH / 1.33 h / 20 °C

With Trimethyl orthoacetate; lithium aluminium tetrahydride; mercury(II) perchlorate; methyldiethoxyborane; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; 10-camphorsufonic acid; tert.-butyl lithium; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; ethylenediamine; diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; pentane;

DOI:10.1021/ol017261d

upstream raw materials:

methyl 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-6,8-O-isopropylidene-1-undecenyl]-6-methoxybenzoate

methyl 2-methoxy-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate

5-oxo-tetrahydro-furan-2-carboxylic acid

1-methoxy-3-tetrahydropyran-2-yloxybenzene

Downstream raw materials:

2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoic acid

(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one