benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

Base Information

• Chemical Name: benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester
• CAS No.: 588693-55-4
• Molecular Formula: C₄₁H₅₄O₇Si₂
• Molecular Weight: 715.047
• Mol file: 588693-55-4.mol

Synonyms:benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

Chemical Property of benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

There total 3 articles about benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl 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: 92.0%

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-5-oxo-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester (588693-53-2) → benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester (588693-55-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ja0342998

Reference yield:

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester (1026979-90-7) → benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester (588693-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 10.76 g / DMAP; Cl₃CCOCl / pyridine / 10 h / 20 °C

2: 92 percent / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.25 h / -78 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; trifluoroacetyl chloride; In pyridine; methanol; dichloromethane; 2: Luche's reduction;

DOI:10.1021/ja0342998

Reference yield:

benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester (1026479-97-9) → benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester (588693-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: n-Bu₄NF / tetrahydrofuran; H₂O / 7 h / 0 °C

2: 10.76 g / DMAP; Cl₃CCOCl / pyridine / 10 h / 20 °C

3: 92 percent / CeCl₃*7H₂O; NaBH₄ / methanol; CH₂Cl₂ / 0.25 h / -78 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; trifluoroacetyl chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; 3: Luche's reduction;

DOI:10.1021/ja0342998

upstream raw materials:

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxy-5-oxo-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-3-methoxy-5-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-8-yl ester

benzoic acid 1-{2-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-vinyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-3-(tert-butyl-diphenyl-silanyloxy)-2-oxo-propyl ester

Downstream raw materials:

tetradotoxin

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde

(1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetic acid methyl ester