4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester
• CAS No.: 162061-65-6
• Molecular Formula: C₃₀H₄₁NO₇
• Molecular Weight: 527.658
• Mol file: 162061-65-6.mol

Synonyms:4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester

Chemical Property of 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester

There total 27 articles about 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl 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: 72.0%

(2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-46-4) + 4-nitro-benzoic acid (62-23-7) → 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester (162061-65-6) + (Z)-(2S,4R,9S)-9-Benzyloxy-2,4,6,10-tetramethyl-undec-6-enoic acid methyl ester + (E)-(2S,4R,9S)-9-Benzyloxy-2,4,6,10-tetramethyl-undec-6-enoic acid methyl ester

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; for 17.5h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester (162061-65-6)

Guidance literature:

Multi-step reaction with 19 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

5: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

6: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

7: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

8: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

9: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

10: 93 percent / tetrahydrofuran / 10 h / 70 °C

11: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

12: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

13: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

14: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

15: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

16: 94 percent / tetrahydrofuran / 5 h / 70 °C

17: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

18: 96 percent / concd HCl / methanol / 2 h / 50 °C

19: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-3-(benzyloxy)-4-methylpentanal (160531-15-7) → 4-Nitro-benzoic acid (1S,2R,4S,6S)-1-((S)-2-benzyloxy-3-methyl-butyl)-6-methoxycarbonyl-2,4-dimethyl-heptyl ester (162061-65-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

2: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

3: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

4: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

5: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

6: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

7: 93 percent / tetrahydrofuran / 10 h / 70 °C

8: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

9: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

10: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

11: 88 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

12: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

13: 94 percent / tetrahydrofuran / 5 h / 70 °C

14: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

15: 96 percent / concd HCl / methanol / 2 h / 50 °C

16: Ph₃P, 1.0 M (EtOOCN)2, p-nitrobenzoic acid / diethyl ether / 17.5 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81206-0

upstream raw materials:

(2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester

4-nitro-benzoic acid

4-methylpent-2-en-1-ol

(S)-4-methyl-pentane-1,3-diol

Downstream raw materials:

(2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid

[(2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoylamino]-acetic acid tert-butyl ester

(3R,9S,11S,13R,14S,16S)-3-[(4-{[tert-butyl(dimethyl)silyl]oxy}-3-iodophenyl)methyl]-14-hydroxy-4,9,11,13-tetramethyl-16-(propan-2-yl)-1-oxa-4,7-diazacyclohexadecane-2,5,8-trione

Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester