erythro-N^α-(benzyloxy)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-(benzyloxy)carbonyl-N^im-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester
• CAS No.: 170375-02-7
• Molecular Formula: C₄₇H₄₉N₃O₁₃
• Molecular Weight: 863.918

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

There total 6 articles about erythro-N^α-(benzyloxy)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: 65.0%

Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidine methyl ester (160054-29-5,170375-01-6) + 3,4,6-tri-O-acetyl-2-O-methyl-β-L-gulopyranosyl diphenyl phosphate (170375-00-5) → erythro-Nα-(benzyloxy)carbonyl-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-02-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -16 ℃; for 0.5h;

Reference yield:

Benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (78355-19-8) → erythro-Nα-(benzyloxy)carbonyl-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-02-7)

Guidance literature:

Multi-step reaction with 6 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

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

Reference yield:

benzyl 3,4,6-tri-O-benzyl-2-O-methyl-β-L-gulopyranoside (170374-98-8) → erythro-Nα-(benzyloxy)carbonyl-Nim-(triphenylmethyl)-β-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester (170375-02-7)

Guidance literature:

Multi-step reaction with 5 steps

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

2: pyridine / 24 h / 25 °C

3: 59 percent / BnNH₂ / tetrahydrofuran / 6 h / 25 °C

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

5: 65 percent / TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -16 °C

With pyridine; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; hydrogen; benzylamine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

N^α-((benzyloxy)carbonyl)-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidine methyl ester

3,4,6-tri-O-acetyl-2-O-methyl-β-L-gulopyranosyl diphenyl phosphate

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-(3,4,6-tri-O-acetyl-2-O-methyl-α-L-gulopyranosyl)-L-histidine methyl ester

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

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