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

Base Information

• Chemical Name: (2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid
• CAS No.: 162061-66-7
• Molecular Formula: C₂₈H₅₀O₄Si
• Molecular Weight: 478.788
• Mol file: 162061-66-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 43 articles about (2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid 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: 83.0%

C28H52O3Si → (2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid (162061-66-7)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; acetonitrile; at 35 ℃; for 7h; pH=6; Inert atmosphere;

DOI:10.1002/chem.201501252

Reference yield:

(S)-3-(benzyloxy)-4-methylpentanal (160531-15-7) → (2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid (162061-66-7)

Guidance literature:

Multi-step reaction with 19 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

17: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

18: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

19: K₂CO₃ / CH₂Cl₂; methanol; tetrahydrofuran; H₂O / 1 h / 40 °C

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

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

Reference yield:

C34H64O4Si2 → (2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid (162061-66-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; at 40 ℃; for 1h; Yield given;

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

upstream raw materials:

t-butyldimethylsiyl triflate

4-methylpent-2-en-1-ol

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

benzyl bromide

Downstream raw materials:

(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

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

deiododoliculide silyl ether