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

Base Information

• Chemical Name: erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine
• CAS No.: 170375-12-9
• Molecular Formula: C₃₆H₄₁N₃O₁₀
• Molecular Weight: 675.736

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 7 articles about erythro-N^α-((tert-butyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(α-D-mannopyranosyl)-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: 67.0%

erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-11-8) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine (170375-12-9)

Guidance literature:

With lithium hydroxide; In methanol; at 4 ℃; for 3h;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine (170375-12-9)

Guidance literature:

Multi-step reaction with 5 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

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → erythro-Nα-((tert-butyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(α-D-mannopyranosyl)-L-histidine (170375-12-9)

Guidance literature:

Multi-step reaction with 6 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

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; 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-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

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:

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

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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