Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester
CAS No.:674769-38-1
Molecular Formula:C₃₂H₄₂O₇
Molecular Weight:538.681
Hs Code.:

Synonyms:Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

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Chemical Property of Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

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Technology Process of Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

There total 15 articles about Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl 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: 82.0%

: 674769-43-8
Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

: 674769-38-1
Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

Guidance literature:: With copper; zinc; In ethanol;
DOI:10.1021/ol036393z

Reference yield:

: 5072-70-8
1-bromo-2,3-dimethyl-2-butene

: 674769-38-1
Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 69 percent / SnCl₂*H₂O; NaI

2: 99 percent / LDA

3: BF₃*Et₂O / CH₂Cl₂ / -20 - 0 °C

4: 90 percent / proton sponge

5: 82 percent / Zn; Cu / ethanol

With Proton Sponge; boron trifluoride diethyl etherate; copper; sodium iodide; tin(ll) chloride; zinc; lithium diisopropyl amide; In ethanol; dichloromethane; 1: Barbier-type reaction / 1: Swern oxidation / 3: Mukaiyama aldol reaction / 5: Vasella ring cleavage;
DOI:10.1021/ol036393z

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 674769-38-1
Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: TsOH

2.1: 90 percent / NaH

3.1: 99 percent / NBS; BaCO₃ / CCl₄ / Heating

4.1: 95 percent / TMSOTf / acetonitrile / -20 °C

5.1: OsO₄; NMO

5.2: 96 percent / NaIO₄

6.1: BF₃*Et₂O / CH₂Cl₂ / -20 - 0 °C

7.1: 90 percent / proton sponge

8.1: 82 percent / Zn; Cu / ethanol

With N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; Proton Sponge; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; copper; sodium hydride; toluene-4-sulfonic acid; barium carbonate; zinc; In tetrachloromethane; ethanol; dichloromethane; acetonitrile; 6.1: Mukaiyama aldol reaction / 8.1: Vasella ring cleavage;
DOI:10.1021/ol036393z