[2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone

Base Information

• Chemical Name: [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone
• CAS No.: 500734-32-7
• Molecular Formula: C₄₄H₆₀Cl₂N₄O₉SSi
• Molecular Weight: 920.039

Synonyms:

Chemical Property of [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone

Chemical Property:

Purity/Quality:

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Technology Process of [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone

There total 23 articles about [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1⁽²¹⁾,18-diene-4,7,10,13,17-pentaone 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:

2-((S)-1-Amino-2-methyl-propyl)-thiazole-4-carboxylic acid (S)-1-(1-{(S)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-hydroxy-2-methyl-propoxycarbonyl}-1-methyl-ethyl)-5,5-dichloro-hexyl ester; hydrochloride → [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1(21),18-diene-4,7,10,13,17-pentaone (500734-32-7)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)01224-3

Reference yield:

benzyl 3-methylbut-2-enoate (37526-89-9) → [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1(21),18-diene-4,7,10,13,17-pentaone (500734-32-7)

Guidance literature:

Multi-step reaction with 9 steps

1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol

2: H₂ / 5 percent Pd/C / tetrahydrofuran / 0.5 h / 20 °C / 760 Torr

3: 129 mg / KHCO₃ / dimethylformamide / 7 h / 20 °C

4: 66 percent / 2,4,6-trichlorobenzoyl chloride; triethylamine; DMAP / toluene / 12 h / 60 °C

5: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 20 °C

6: 42 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 17 h / 20 °C

7: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 20 °C

8: HCl / ethyl acetate; H₂O / 0.5 h / 20 °C

9: 15 mg / pentafluorophenyl diphenylphosphinate; i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C

With morpholine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonamide; diethyl cyanophosphonate; AD-mix-β; 2,4,6-trichlorobenzoyl chloride; pentafluorophenyl diphenyl-phosphinate; hydrogen; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Sharpless reaction;

DOI:10.1016/S0040-4020(02)01224-3

Reference yield:

benzyl (2S)-2,3-dihydroxy-3-methylbutanoate (176505-53-6) → [2S,8R,11S,15S]-8-(tert-butyldiphenylsilanyloxymethyl)-15-(4,4-dichloropentyl)-11-(1-hydroxy-1-methyl-ethyl)-2-isopropyl-14,14-dimethyl-12,16-dioxa-20-thia-3,6,9,21-tetraaza-bicyclo[16.2.1]heneicosa-1(21),18-diene-4,7,10,13,17-pentaone (500734-32-7)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 5 percent Pd/C / tetrahydrofuran / 0.5 h / 20 °C / 760 Torr

2: 129 mg / KHCO₃ / dimethylformamide / 7 h / 20 °C

3: 66 percent / 2,4,6-trichlorobenzoyl chloride; triethylamine; DMAP / toluene / 12 h / 60 °C

4: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 20 °C

5: 42 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 17 h / 20 °C

6: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 20 °C

7: HCl / ethyl acetate; H₂O / 0.5 h / 20 °C

8: 15 mg / pentafluorophenyl diphenylphosphinate; i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C

With morpholine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl cyanophosphonate; 2,4,6-trichlorobenzoyl chloride; pentafluorophenyl diphenyl-phosphinate; hydrogen; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(02)01224-3

upstream raw materials:

t-Boc-L-valine

benzyl 3-methylbut-2-enoate

(S)-N-tert-butoxycarbonylvalinal

tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate

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