(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

Base Information

• Chemical Name: (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid
• CAS No.: 146388-31-0
• Molecular Formula: C₅₃H₅₂N₄O₁₂
• Molecular Weight: 937.015

Synonyms:(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

Chemical Property of (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

Chemical Property:

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Technology Process of (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

There total 26 articles about (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic 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: 95.0%

(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(19),2(21),3,5,16(20),17-hexaene-8-carboxylic acid methyl ester (146388-30-9) → (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(19),2(21),3,5,16(20),17-hexaene-8-carboxylic acid (146388-31-0)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 10 ℃; for 2h;

DOI:10.1055/s-1992-26351

Reference yield:

2-benzyloxy-5-bromobenzaldehyde (121124-94-5) → (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(19),2(21),3,5,16(20),17-hexaene-8-carboxylic acid (146388-31-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 1) Sn(OTf)2, N-ethylpiperidine / 1) THF, -78 deg C, 90 min, 2) 2 h

2: 90 percent / MeMgBr / diethyl ether; CH₂Cl₂ / 0.05 h / 0 °C

3: 90 percent / DMAP / CH₂Cl₂ / 0.17 h

4: 30percent H₂O₂, HCO₂H / CH₂Cl₂ / 0.5 h / 0 °C

5: 2) 2M Na₂CO₃ / 1) Pd(PPh₃)4 / 1) THF, 1 h, reflux, 2) 24 h, reflux

6: 80 percent / Cs₂CO₃ / methanol / 2 h / Ambient temperature

7: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h

8: 85 percent / H₂ / (R,R)-BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature

9: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

10: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT

11: 71 percent / HOAc / H₂O / 4 h / 50 °C

12: 96 percent / Bu₄NF*3H₂O / dimethylformamide / 2 h / Ambient temperature

13: EDCI / CH₂Cl₂ / 15 h / -10 deg C to RT

14: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

15: aq. KHCO₃ / CHCl₃ / 1) RT, 2 h, 2) 50 deg C, 30 min

16: 95 percent / 1M LiOH / H₂O; dioxane / 2 h / 10 °C

With 1-ethyl-piperidine; hydrogenchloride; dmap; lithium hydroxide; tin(II) trifluoromethanesulfonate; formic acid; 1,1,3,3-tetramethylguanidine; methylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium carbonate; benzotriazol-1-ol; potassium hydrogencarbonate; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1055/s-1992-26351

Reference yield:

2-benzyloxy-5-iodobenzaldehyde (134038-89-4) → (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(19),2(21),3,5,16(20),17-hexaene-8-carboxylic acid (146388-31-0)

Guidance literature:

Multi-step reaction with 18 steps

1: 92 percent / NaClO₄, amidosulfonic acid / H₂O; dioxane / 0.5 h / Ambient temperature

2: 98 percent / methanol; diethyl ether

4: 90 percent / LiOH*H₂O / dioxane; H₂O / 1) RT, 5 h, ultrasound, 2) 50 deg C, 15 h

5: 1-chloro-1-(N,N-dimethylamino)-2-methyl-1-propene / CH₂Cl₂ / 0.25 h / 0 °C

6: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h

7: H₂ / <(R)-(RuCl(p-cymene)BINAP>Cl / methanol; CH₂Cl₂ / 72 h / 50 °C / 37503 Torr

8: 97 percent / aq. HOAc / 3 h / 50 °C

9: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h

10: 85 percent / H₂ / (R,R)-BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature

11: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

12: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 15 h / -10 deg C to RT

13: 71 percent / HOAc / H₂O / 4 h / 50 °C

14: 96 percent / Bu₄NF*3H₂O / dimethylformamide / 2 h / Ambient temperature

15: EDCI / CH₂Cl₂ / 15 h / -10 deg C to RT

16: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

17: aq. KHCO₃ / CHCl₃ / 1) RT, 2 h, 2) 50 deg C, 30 min

18: 95 percent / 1M LiOH / H₂O; dioxane / 2 h / 10 °C

With hydrogenchloride; lithium hydroxide; n-butyllithium; 1,1,3,3-tetramethylguanidine; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; aminosulfonic acid; sodium perchlorate; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; potassium hydrogencarbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ((+)-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1055/s-1992-26351

upstream raw materials:

(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid methyl ester

2-benzyloxy-5-bromobenzaldehyde

2-benzyloxy-5-iodobenzaldehyde

2-(2-(benzyloxy)-5-bromophenyl)-1,3-dioxane

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