N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr

Base Information

• Chemical Name: N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr
• CAS No.: 170375-13-0
• Molecular Formula: C₆₀H₇₈N₉O₁₄S₃
• Molecular Weight: 1245.53

Synonyms:N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr

Chemical Property of N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr

Chemical Property:

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Safty Information:

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Useful:

Technology Process of N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr

There total 8 articles about N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr 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: 64.0%

{3-[(2'-{2-[(2S,3R)-2-((2S,3S,4R)-4-Amino-3-hydroxy-2-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-ethyl}-[2,4']bithiazolyl-4-carbonyl)-amino]-propyl}-dimethyl-sulfonium + erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine (170375-12-9) → Nα-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-Nim-(triphenylmethyl)-erythr (170375-13-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 10h;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → Nα-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-Nim-(triphenylmethyl)-erythr (170375-13-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / NaH / CH₂Cl₂ / 0.25 h / 25 °C

2: 24 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

3: 71 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 25 °C / 760 Torr

4: 99 percent / aq. NaHCO₃ / tetrahydrofuran / 1.5 h / 25 °C

5: 67 percent / 0.1 N aq. LiOH / methanol / 3 h / 4 °C

6: 64 percent / DCC, HOBT / dimethylformamide / 10 h / 25 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → Nα-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-Nim-(triphenylmethyl)-erythr (170375-13-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / BnNH₂

2: 69 percent / NaH / CH₂Cl₂ / 0.25 h / 25 °C

3: 24 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

4: 71 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 25 °C / 760 Torr

5: 99 percent / aq. NaHCO₃ / tetrahydrofuran / 1.5 h / 25 °C

6: 67 percent / 0.1 N aq. LiOH / methanol / 3 h / 4 °C

7: 64 percent / DCC, HOBT / dimethylformamide / 10 h / 25 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; benzylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)erythro-β-(α-D-gulopyranosyl)-L-histidi

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