erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

Base Information

• Chemical Name: erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester
• CAS No.: 170375-04-9
• Molecular Formula: C₄₄H₅₁N₃O₁₃
• Molecular Weight: 829.901

Synonyms:erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

Chemical Property of erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

There total 8 articles about erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl 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: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + erythro-Nim-(triphenylmethyl)-β-(2,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-03-8) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-04-9)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 25 ℃; for 3h;

Reference yield:

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-04-9)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; benzylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

Reference yield:

(2S,3S,4S,5S,6S)-6-Hydroxymethyl-3-methoxy-tetrahydro-pyran-2,4,5-triol → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-04-9)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; benzylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

erythro-N^im-(triphenylmethyl)-β-(2,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

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

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

Downstream 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

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)

erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(2-O-methyl-α-L-gulopyranosyl)-L-histidine

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