(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Base Information

Chemical Name:(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester
CAS No.:146968-13-0
Molecular Formula:C₅₂H₈₀O₁₅
Molecular Weight:945.198
Hs Code.:

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Synonyms:(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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Chemical Property of (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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Technology Process of (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

There total 4 articles about (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl 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: 73.0%

: 123-62-6
propionic acid anhydride

: 146968-12-9
<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(4-hydroxy-5-methyl-3-methylene-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) 7-(1-methoxy-1-methylethyl ether) ester

: 146968-13-0
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1021/jm00049a022

Reference yield:

: 138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4
zaragozic acid A

: 146968-13-0
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / toluene / 16 h / 65 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

3: cerium(III) chloride, ethylmagnesium chloride / tetrahydrofuran / 0.83 h / -78 °C

4: 73 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With dmap; cerium(III) chloride; ethylmagnesium chloride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jm00049a022

Reference yield:

: 144358-24-7
<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

: 146968-13-0
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: cerium(III) chloride, ethylmagnesium chloride / tetrahydrofuran / 0.83 h / -78 °C

3: 73 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With dmap; cerium(III) chloride; ethylmagnesium chloride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm00049a022