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

Base Information

Chemical Name:(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one
CAS No.:186768-34-3
Molecular Formula:C₃₇H₅₂O₉
Molecular Weight:640.814
Hs Code.:

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

Synonyms:(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-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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Chemical Property of (E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-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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Technology Process of (E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

There total 3 articles about (E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-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: 43.0%

: 186768-33-2
(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

: 186768-34-3
(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1002/jlac.199719970135

Reference yield:

: 164735-19-7
5-O-(4-methoxybenzyl)soraphen

: 186768-34-3
(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 55 percent / pyridine; SOCl₂ / 0.75 h

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

3: 43 percent / NaBH₄ / tetrahydrofuran; various solvent(s) / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; thionyl chloride; phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;
DOI:10.1002/jlac.199719970135

Reference yield:

: 186768-32-1
(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

: 186768-34-3
(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-18-Hydroxy-1,10,11-trimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

Guidance literature:: Multi-step reaction with 2 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

With sodium tetrahydroborate; phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;
DOI:10.1002/jlac.199719970135