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

Base Information

Chemical Name:Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester
CAS No.:161978-96-7
Molecular Formula:C₃₇H₅₈N₄O₆SSi
Molecular Weight:715.042
Hs Code.:

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

Synonyms:Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

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Chemical Property of Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

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Technology Process of Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

There total 23 articles about Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} 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:

: 160531-20-4
(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid methyl ester

: 161978-96-7
Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

Guidance literature:: Multi-step reaction with 18 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

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium acetate; 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:

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

: 161978-96-7
Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

Guidance literature:: Multi-step reaction with 7 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

With dmap; hydrogen; sodium acetate; 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;
DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

: 160531-43-1
(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid methyl ester

: 161978-96-7
Imidazole-1-carbothioic acid O-{(3R,9S,11S,13R,14S,16S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl} ester

Guidance literature:: Multi-step reaction with 14 steps

1: 94 percent / tetrahydrofuran / 5 h / 70 °C

2: 76 percent / Bu₃SnH / toluene / 0.17 h / Heating

3: 96 percent / concd HCl / methanol / 2 h / 50 °C

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

5: 52.0 mg / 20percent (w/w) aq. NaOH / methanol / 2 h / 45 °C

6: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

8: 98 percent / DEPC, Et₃N / dimethylformamide / 0.5 h / 0 °C

9: 95 percent / H₂ / 20percent Pd(OH)2/C / dioxane / 1.5 h / 40 °C / 760 Torr

10: 94 percent / 4-dimethylaminopyridine, DCC / CH₂Cl₂ / 2 h / -20 °C

11: CH₂Cl₂ / 3 h / Ambient temperature

12: 74 percent / Bop-Cl, Et₃N / CH₂Cl₂ / 0 to 25 deg C, 6 h; 25 deg C, 13 h

13: 92 percent / H₂, NaOAc / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

14: 85 percent / tetrahydrofuran / 5 h / Heating

With hydrogenchloride; dmap; sodium hydroxide; hydrogen; tri-n-butyl-tin hydride; sodium acetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; 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