methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Base Information

Chemical Name:methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate
CAS No.:144108-04-3
Molecular Formula:C₃₃H₅₀O₉Si
Molecular Weight:618.84
Hs Code.:

Synonyms:methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

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Chemical Property of methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

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Technology Process of methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

There total 3 articles about methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate 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: 71.0%

: 111436-88-5
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propionaldehyde

: 144108-03-2
dimethyl <3-<5'-(allyloxy)-2'-carbomethoxy-3'-hydroxyphenyl>-2-oxopropyl>phosphonate

: 6-Allyloxy-3-[(E)-(3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-1-enyl]-8-hydroxy-isochromen-1-one

: 144108-04-3
methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at -10 ℃; for 24h;
DOI:10.1021/jo00050a047

Reference yield:

: 6110-30-1
methyl <3,5-dihydroxy-2-(methoxycarbonyl)phenyl>acetate

: 144108-04-3
methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / K₂CO₃*1.5 H₂O / acetone / 6 h / Heating

2: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3: 71 percent / LiCl, DBU / acetonitrile / 24 h / -10 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexane; acetone; acetonitrile;
DOI:10.1021/jo00050a047

Reference yield:

: 144108-02-1
methyl <5-(allyloxy)-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate

: 144108-04-3
methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C

2: 71 percent / LiCl, DBU / acetonitrile / 24 h / -10 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexane; acetonitrile;
DOI:10.1021/jo00050a047