(-)-methyl 4,5-O-benzylidene-4-epi-shikimate

Base Information Edit

Chemical Name:(-)-methyl 4,5-O-benzylidene-4-epi-shikimate
CAS No.:94903-41-0
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:
Mol file:94903-41-0.mol

Synonyms:(-)-methyl 4,5-O-benzylidene-4-epi-shikimate

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Chemical Property of (-)-methyl 4,5-O-benzylidene-4-epi-shikimate Edit

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Technology Process of (-)-methyl 4,5-O-benzylidene-4-epi-shikimate

There total 10 articles about (-)-methyl 4,5-O-benzylidene-4-epi-shikimate 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: 92.0%

: 94843-97-7
(1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene

: 94903-41-0
(-)-methyl 4,5-O-benzylidene-4-epi-shikimate

Guidance literature:: With sodium methylate; In methanol; for 1h; Ambient temperature;
DOI:10.1021/jo00206a035

Reference yield: 72.0%

: 4372-89-8,4372-91-2,14671-74-0,16613-43-7,16613-44-8,40983-58-2,121468-33-5,141781-68-2
methyl 4-epi-shikimate

: 100-52-7
benzaldehyde

: 80631-78-3,80631-88-5,94903-41-0,94903-43-2,116183-40-5
methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In toluene; Heating;
DOI:10.1021/ja00389a025

Reference yield:

: 78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6
(1S,6R)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

: 80631-78-3,80631-88-5,94903-41-0,94903-43-2,116183-40-5
methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 2.) NaOCH₃ / 1.) reflux, 1.25 h, 2.) MeOH, room temperature, 1.5 h

2: 72 percent / p-toluenesulfonic acid / toluene / Heating

With sodium methylate; toluene-4-sulfonic acid; In toluene;
DOI:10.1021/ja00389a025