4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

Base Information

Chemical Name:4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide
CAS No.:288395-73-3
Molecular Formula:C₂₈H₃₅NO₇Si
Molecular Weight:525.674
Hs Code.:

4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

Synonyms:4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

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Chemical Property of 4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

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Technology Process of 4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

There total 18 articles about 4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide 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:

: 288395-84-6
4-(1-Ethoxy-ethoxy)-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

: 288395-73-3
4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/ja000930i

Reference yield:

: 7797-83-3
2H-benzo[d]1,3-dioxolane-4-carbaldehyde

: 288395-73-3
4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / Heating

1.2: 63 percent / KOH / ethanol / 2 h / 20 °C

2.1: 90 percent / silver trifluoroacetate; Br₂ / CHCl₃ / 1 h / 10 - 15 °C

3.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h

4.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C

4.2: tetrahydrofuran; pentane; toluene / 0.75 h / -100 °C

5.1: NaH / dimethylformamide / 0.5 h / -5 °C

5.2: dimethylformamide / 0.25 h / -5 °C

6.1: 157 mg / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

With n-butyllithium; bromine; silver trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; pentane; 1.1: Rearrangement / 1.2: Hydrolysis / 2.1: Bromination / 3.1: Addition / 4.1: Metallation / 4.2: Addition / 5.1: Metallation / 5.2: Substitution / 6.1: deprotection;
DOI:10.1021/ja000930i

Reference yield:

: 6493-77-2
methyl cyclohex-3-ene-1-carboxylate

: 288395-73-3
4-Hydroxy-benzo[1,3]dioxole-5-carboxylic acid [(1R,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl]-(4-methoxy-benzyl)-amide

Guidance literature:: Multi-step reaction with 12 steps

1.1: N-bromosuccinimide; azobis(isobutyronitrile) / benzene / 0.33 h / Heating

1.2: tri-n-butyltinhydride; azobis(isobutyronitrile) / benzene / 3.5 h / Heating

2.1: O₂; Rose Bengal / acetone / 8 h / -10 °C / Irradiation

2.2: RuCl₂(PPh₃)3 / CH₂Cl₂ / -10 - 20 °C

2.3: 42 percent / NaOMe / methanol / 0.5 h / -5 °C

3.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 80 percent Turnov_. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7

5.1: triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 36 h

6.1: 82 mg / NaOMe / methanol / 1.5 h / 0 - 5 °C

7.1: 100 percent / imidazole / dimethylformamide / 0.67 h / 20 °C

8.1: 84 percent / LiOH*H₂O / methanol / 48 h / -5 °C

9.1: Et₃N; diphenylphosphorazidate / benzene / 1 h

9.2: toluene / 1 h / 110 °C

10.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C

10.2: tetrahydrofuran; pentane; toluene / 0.75 h / -100 °C

11.1: NaH / dimethylformamide / 0.5 h / -5 °C

11.2: dimethylformamide / 0.25 h / -5 °C

12.1: 157 mg / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; cholesterol esterase; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; oxygen; sodium methylate; pyridinium p-toluenesulfonate; rose bengal; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene; 1.1: Bromination / 1.2: Dehydrobromination / 2.1: Oxidation / 2.2: Epoxidation / 2.3: Ring cleavage / 3.1: Acylation / 4.1: Hydrolysis / 5.1: Mitsunobu reaction / 6.1: Deacetylation / 7.1: Addition / 8.1: Hydrolysis / 9.1: azidation / 9.2: Rearrangement / 10.1: Metallation / 10.2: Addition / 11.1: Metallation / 11.2: Substitution / 12.1: deprotection;
DOI:10.1021/ja000930i