Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

Base Information

Chemical Name:Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate
CAS No.:165258-12-8
Molecular Formula:C₄₆H₅₂O₈Si
Molecular Weight:761
Hs Code.:

Synonyms:Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

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Chemical Property of Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

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Technology Process of Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

There total 9 articles about Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate 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: 85.0%

: Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-1'-hydroxy-2',4'-dimethylpent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

: 165258-12-8
Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 23 ℃; for 1h;
DOI:10.1021/jo00119a018

Reference yield:

: 100-39-0
benzyl bromide

: 165258-12-8
Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / Ag₂O / CHCl₃ / 6 h

2: aq. Na₂S₂O₄ / n-Bu₄NBr / tetrahydrofuran / 0.5 h

3: aq. KOH / tetrahydrofuran / 10 h

4: 85 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) -78 deg C, 1 h

5: 97 percent / DBU / acetonitrile / 2 h

6: 94 percent / NBS / H₂SO₄ / tetrahydrofuran / 6 h / 23 °C

7: 70 percent / n-BuLi / tetrahydrofuran / 1.) -100 deg C, 5 min, 2.) -100 deg C, 30 min then -100 to 23 deg C, 1 h

8: 85 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / 0 - 23 °C

With pyridine; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; sodium dithionite; tert.-butyl lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; sulfuric acid; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo00119a018

Reference yield:

: 165258-03-7
3-Bromo-5-hydroxy-7-methoxy-6-methyl-1,4-naphthoquinone

: 165258-12-8
Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / Ag₂O / CHCl₃ / 6 h

2: aq. Na₂S₂O₄ / n-Bu₄NBr / tetrahydrofuran / 0.5 h

3: aq. KOH / tetrahydrofuran / 10 h

4: 85 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) -78 deg C, 1 h

5: 97 percent / DBU / acetonitrile / 2 h

6: 94 percent / NBS / H₂SO₄ / tetrahydrofuran / 6 h / 23 °C

7: 70 percent / n-BuLi / tetrahydrofuran / 1.) -100 deg C, 5 min, 2.) -100 deg C, 30 min then -100 to 23 deg C, 1 h

8: 85 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / 0 - 23 °C

With pyridine; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; sodium dithionite; tert.-butyl lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; sulfuric acid; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo00119a018