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

Base Information

• Chemical Name: erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(2-O-methyl-α-L-gulopyranosyl)-L-histidine
• CAS No.: 170375-05-0
• Molecular Formula: C₃₇H₄₃N₃O₁₀
• Molecular Weight: 689.763

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

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

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-(2-O-methyl-α-L-gulopyranosyl)-L-histidine

There total 10 articles about erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(2-O-methyl-α-L-gulopyranosyl)-L-histidine 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: 62.0%

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) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2-O-methyl-α-L-gulopyranosyl)-L-histidine (170375-05-0)

Guidance literature:

With lithium hydroxide; In methanol; at 4 ℃; for 2.5h;

Reference yield:

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2-O-methyl-α-L-gulopyranosyl)-L-histidine (170375-05-0)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; lithium hydroxide; 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-(2-O-methyl-α-L-gulopyranosyl)-L-histidine (170375-05-0)

Guidance literature:

Multi-step reaction with 7 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

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

upstream raw materials:

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

di-tert-butyl dicarbonate

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:

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)

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

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