erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

Base Information

• Chemical Name: erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester
• CAS No.: 170375-10-7
• Molecular Formula: C₄₀H₄₃N₃O₁₂
• Molecular Weight: 757.794

Synonyms:erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

Chemical Property of erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

There total 5 articles about erythro-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-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: 71.0%

erythro-Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-09-4) → erythro-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-10-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; for 0.75h; under 760 Torr;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → erythro-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-10-7)

Guidance literature:

Multi-step reaction with 3 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

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

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → erythro-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-10-7)

Guidance literature:

Multi-step reaction with 4 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

With trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; benzylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

upstream raw materials:

erythro-N^α-((benzyloxy)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:

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

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

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

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