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-(2'''-O-methyl-α-L-gulop)

Base Information

• Chemical Name: 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-(2'''-O-methyl-α-L-gulop)
• CAS No.: 170375-07-2
• Molecular Formula: C₅₆H₇₂N₉O₁₂S₃
• Molecular Weight: 1159.44

Synonyms: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-(2'''-O-methyl-α-L-gulop)

Chemical Property of 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-(2'''-O-methyl-α-L-gulop)

Chemical Property:

Purity/Quality:

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Technology Process of 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-(2'''-O-methyl-α-L-gulop)

There total 12 articles about 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-(2'''-O-methyl-α-L-gulop) 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: 89.0%

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)-erythro (170375-06-1) → 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)erythro-β-(2'''-O-methyl-α-L-gulop) (170375-07-2)

Guidance literature:

With hydrogenchloride; In acetic acid; at 25 ℃; for 0.0833333h;

Reference yield:

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) → 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)erythro-β-(2'''-O-methyl-α-L-gulop) (170375-07-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) NaH, 3.) NaH

2: H₂ / 20percent Pd(OH)2-C / methanol / 6 h / 25 °C / 760 Torr

3: pyridine / 24 h / 25 °C

4: 59 percent / BnNH₂ / tetrahydrofuran / 6 h / 25 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 15 min

6: 65 percent / TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -16 °C

7: 77 percent / H₂ / 10percent Pd/C / methanol / 0.67 h / 25 °C / 760 Torr

8: 94 percent / aq. NaHCO₃ / tetrahydrofuran / 3 h / 25 °C

9: 62 percent / 0.1 N aq. LiOH / methanol / 2.5 h / 4 °C

10: 76 percent / DCC, HOBt, NaHCO₃ / dimethylformamide / 22 h / 25 °C

11: 89 percent / 1N aq. HCl / acetic acid / 0.08 h / 25 °C

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

Reference yield:

(2S,3S,4S,5S,6S)-6-Hydroxymethyl-3-methoxy-tetrahydro-pyran-2,4,5-triol → 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)erythro-β-(2'''-O-methyl-α-L-gulop) (170375-07-2)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 24 h / 25 °C

2: 59 percent / BnNH₂ / tetrahydrofuran / 6 h / 25 °C

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 15 min

4: 65 percent / TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -16 °C

5: 77 percent / H₂ / 10percent Pd/C / methanol / 0.67 h / 25 °C / 760 Torr

6: 94 percent / aq. NaHCO₃ / tetrahydrofuran / 3 h / 25 °C

7: 62 percent / 0.1 N aq. LiOH / methanol / 2.5 h / 4 °C

8: 76 percent / DCC, HOBt, NaHCO₃ / dimethylformamide / 22 h / 25 °C

9: 89 percent / 1N aq. HCl / acetic acid / 0.08 h / 25 °C

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

upstream raw materials:

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)-erythro

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside

3,4,6-tri-O-acetyl-2-O-methyl-β-L-gulopyranose

1,3,4,6-tetra-O-acetyl-2-O-methyl-β-L-gulopyranose

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