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

Base Information

• Chemical Name: (2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester
• CAS No.: 160531-46-4
• Molecular Formula: C₂₃H₃₈O₄
• Molecular Weight: 378.552
• Mol file: 160531-46-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 25 articles about (2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl 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: 96.0%

(2S,4S,6R,7R,9S)-9-Benzyloxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-22-6) → (2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-46-4)

Guidance literature:

With hydrogenchloride; In methanol; at 50 ℃; for 2h;

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

Reference yield:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → (2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-46-4)

Guidance literature:

Multi-step reaction with 18 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

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; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

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

Reference yield:

(S)-3-Benzyloxy-4-methyl-pentan-1-ol (160531-37-3) → (2S,4S,6R,7R,9S)-9-Benzyloxy-7-hydroxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester (160531-46-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

2: 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

3: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

4: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

5: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

6: 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

7: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

8: 93 percent / tetrahydrofuran / 10 h / 70 °C

9: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

10: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

11: 98 percent / DMSO, (COCl)2; Et₃N / CH₂Cl₂ / -78 °C / -78 deg C, 10 min; -78 to 0 deg C, 0 deg C, 10 min

12: 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

13: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

14: 94 percent / tetrahydrofuran / 5 h / 70 °C

15: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

16: 96 percent / concd HCl / methanol / 2 h / 50 °C

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; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

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

upstream raw materials:

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

4-methylpent-2-en-1-ol

ethyl 4-methylpent-2-enoate

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

Downstream raw materials:

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

(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