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

Base Information

• Chemical Name: Dithiocarbonic acid O-[(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-1-hydroxy-10,11-dimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-18-yl] ester S-methyl ester
• CAS No.: 186768-46-7
• Molecular Formula: C₃₈H₅₂O₉S₂
• Molecular Weight: 716.957

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

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

5-O-(4-methoxybenzyl)soraphen (164735-19-7) → Dithiocarbonic acid O-[(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-1-hydroxy-10,11-dimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-18-yl] ester S-methyl ester (186768-46-7)

Guidance literature:

Multi-step reaction with 5 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

4: 90 percent / 1 M aq. HCl / tetrahydrofuran / Ambient temperature

5: 1.) 1 M KOH / 1.) DMSO, r.t., 22 h, 2.) r.t., 48 h

With pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

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) → Dithiocarbonic acid O-[(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-1-hydroxy-10,11-dimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-18-yl] ester S-methyl ester (186768-46-7)

Guidance literature:

Multi-step reaction with 4 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: 1.) 1 M KOH / 1.) DMSO, r.t., 22 h, 2.) r.t., 48 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; phosphate buffer; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1002/jlac.199719970135

Reference yield:

(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 (186768-34-3) → Dithiocarbonic acid O-[(E)-(1R,2S,5S,10S,11R,14S,15S,16R,17S,18S)-1-hydroxy-10,11-dimethoxy-17-(4-methoxy-benzyloxy)-2,14,16-trimethyl-3-oxo-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-18-yl] ester S-methyl ester (186768-46-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 1.) 1 M KOH / 1.) DMSO, r.t., 22 h, 2.) r.t., 48 h

With hydrogenchloride; potassium hydroxide; In tetrahydrofuran;

DOI:10.1002/jlac.199719970135

upstream raw materials:

carbon disulfide

(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

methyl iodide

5-O-(4-methoxybenzyl)soraphen

Downstream raw materials:

(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

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