5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

Base Information

Chemical Name:5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone
CAS No.:165258-15-1
Molecular Formula:C₄₈H₅₇NO₈Si₂
Molecular Weight:832.153
Hs Code.:

5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-<N-<<2''-(trimethylsilyl)ethoxy>carbonyl>amino>-1,4-naphthoquinone

Synonyms:5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

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Chemical Property of 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

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Technology Process of 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

There total 11 articles about 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone 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%

: 165258-14-0
5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methyl-3-carbonyl>amino>naphthalene

: 165258-15-1
5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 0.25h;
DOI:10.1021/jo00119a018

Reference yield:

: 100-39-0
benzyl bromide

: 165258-15-1
5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

Guidance literature:: Multi-step reaction with 11 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

9: 92 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 18 h / 23 °C

10: 87 percent / (PhO)2PON₃, Et₃N / tetrahydrofuran / 16 h / Heating

11: 85 percent / aq. ceric ammonium nitrate / acetonitrile / 0.25 h / 0 °C

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

Reference yield:

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

: 165258-15-1
5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone

Guidance literature:: Multi-step reaction with 11 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

9: 92 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 18 h / 23 °C

10: 87 percent / (PhO)2PON₃, Et₃N / tetrahydrofuran / 16 h / Heating

11: 85 percent / aq. ceric ammonium nitrate / acetonitrile / 0.25 h / 0 °C

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