deoxydoliculide silyl ether

Base Information

• Chemical Name: deoxydoliculide silyl ether
• CAS No.: 161978-98-9
• Molecular Formula: C₃₃H₅₅IN₂O₅Si
• Molecular Weight: 714.8
• Mol file: 161978-98-9.mol

Synonyms:deoxydoliculide silyl ether

Chemical Property of deoxydoliculide silyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of deoxydoliculide silyl ether

There total 26 articles about deoxydoliculide silyl ether 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: 78.0%

(3R,9S,11S,13S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione (161978-97-8) → deoxydoliculide silyl ether (161978-98-9)

Guidance literature:

With iodine; mercury(II) trifluoroacetate; In dichloromethane; for 0.75h; Ambient temperature;

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

Reference yield:

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid methyl ester (160531-20-4) → deoxydoliculide silyl ether (161978-98-9)

Guidance literature:

Multi-step reaction with 20 steps

1: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

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

3: 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

4: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1 h, 2.) CHCl₃, Et₂O

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

6: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

7: 96 percent / concd HCl / methanol / 2 h / 50 °C

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

9: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

10: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

12: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

13: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

14: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

15: CH₂Cl₂ / 3 h / Ambient temperature

16: 74 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

17: 92 percent / H₂, NaOAc / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

18: 85 percent / tetrahydrofuran / 5 h / Heating

19: 85 percent / Bu₃SnH / toluene / 0.08 h / Heating

20: 78 percent / I₂, Hg(O₂CCF₃)2 / CH₂Cl₂ / 0.75 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium acetate; mercury(II) trifluoroacetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethyl dicarbonate; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

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

Reference yield:

(2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid (162061-66-7) → deoxydoliculide silyl ether (161978-98-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

2: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

3: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

4: CH₂Cl₂ / 3 h / Ambient temperature

5: 74 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

6: 92 percent / H₂, NaOAc / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

7: 85 percent / tetrahydrofuran / 5 h / Heating

8: 85 percent / Bu₃SnH / toluene / 0.08 h / Heating

9: 78 percent / I₂, Hg(O₂CCF₃)2 / CH₂Cl₂ / 0.75 h / Ambient temperature

With dmap; hydrogen; iodine; tri-n-butyl-tin hydride; sodium acetate; mercury(II) trifluoroacetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; diethyl dicarbonate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

(3R,9S,11S,13S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanal