(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

Base Information

Chemical Name:(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester
CAS No.:156479-53-7
Molecular Formula:C₃₄H₄₂O₁₀
Molecular Weight:610.701
Hs Code.:

Synonyms:(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

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Chemical Property of (5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

Chemical Property:

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Technology Process of (5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

There total 9 articles about (5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl 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: 84.0%

: C₃₇H₄₆O₁₀

: 156479-53-7
(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

Guidance literature:: With trifluoroacetic acid; at 0 ℃;
DOI:10.1016/S0040-4039(00)79967-9

Reference yield:

: 1720-37-2
2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

: 156479-53-7
(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: BuLi / tetrahydrofuran; various solvent(s) / Heating

2: tetrahydrofuran; various solvent(s) / 0 °C

3: 74 percent / TsOH / methanol / Heating

4: 1.) (COCl)2, DMSO 2.) Et₃N

5: 94 percent / NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: 93 percent / HCl

7: 98 percent / H₂ / Pd/CaCO₃ / benzene

8: 84 percent / 80percent aq.TFA / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)79967-9

Reference yield:

: 928-90-5
5-hexyl-1-ol

: 156479-53-7
(5Z,13Z)-(8R,9S,10S,11R)-8,11-Bis-benzoyloxy-9,10-dihydroxy-octadeca-5,13-dienedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / TsOH / CH₂Cl₂

2: BuLi / tetrahydrofuran; various solvent(s) / Heating

3: tetrahydrofuran; various solvent(s) / 0 °C

4: 74 percent / TsOH / methanol / Heating

5: 1.) (COCl)2, DMSO 2.) Et₃N

6: 94 percent / NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

7: 93 percent / HCl

8: 98 percent / H₂ / Pd/CaCO₃ / benzene

9: 84 percent / 80percent aq.TFA / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; Lindlar's catalyst; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)79967-9