(E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,12-dien-3-one

Base Information

• Chemical Name: (E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,12-dien-3-one
• CAS No.: 186768-32-1
• Molecular Formula: C₃₇H₅₀O₈
• Molecular Weight: 622.799

Synonyms:

Chemical Property of (E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,12-dien-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,12-dien-3-one

There total 1 articles about (E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,12-dien-3-one 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: 55.0%

5-O-(4-methoxybenzyl)soraphen (164735-19-7) → (E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1(18),12-dien-3-one (186768-32-1)

Guidance literature:

With pyridine; thionyl chloride; for 0.75h;

DOI:10.1002/jlac.199719970135

Reference yield: 71.0%

(E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1(18),12-dien-3-one (186768-32-1) → (E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S)-1,10,11-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-ene-3,18-dione (186768-33-2)

Guidance literature:

With phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1002/jlac.199719970135

Reference yield:

(E)-(2S,5S,10S,11R,14S,15S,16R,17S)-10,11,18-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadeca-1(18),12-dien-3-one (186768-32-1) → (E)-(1S,6S,11S,12R,15S,16S,17R,18S)-2-Hydroxy-11,12-dimethoxy-18-(4-methoxy-benzyloxy)-3,15,17-trimethyl-6-phenyl-5,19-dioxa-bicyclo[14.2.1]nonadec-13-en-4-one

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / m-chloroperbenzoic acid, phosphate buffer / tetrahydrofuran / 2 h / Ambient temperature

2: 43 percent / NaBH₄ / tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

3: 90 percent / 1 M aq. HCl / tetrahydrofuran / Ambient temperature

4: 98 percent / Et₃N / tetrahydrofuran / 0.33 h / Ambient temperature

5: 25 percent / NaBH₄ / dimethylsulfoxide / 1 h / 60 °C

With hydrogenchloride; sodium tetrahydroborate; phosphate buffer; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1002/jlac.199719970135

upstream raw materials:

5-O-(4-methoxybenzyl)soraphen

Downstream raw materials:

(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S)-1,10,11-Trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-ene-3,18-dione

(E)-(1S,2S,5S,10S,11R,14S,15S,16S,17R)-1,17-Dihydroxy-10,11-dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

Dithiocarbonic acid O-((E)-(1R,2S,5S,10S,11R,14S,15S,16S,17S,18S)-1,17-dihydroxy-10,11-dimethoxy-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-18-yl) ester S-methyl ester

(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-1,18-Dihydroxy-10,11-dimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

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