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

Base Information

• Chemical Name: erythro-N^α-((benzyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester
• CAS No.: 170375-09-4
• Molecular Formula: C₄₈H₄₉N₃O₁₄
• Molecular Weight: 891.929
• Mol file: 170375-09-4.mol

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

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

There total 4 articles about erythro-N^α-((benzyloxy)carbonyl)-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: 32.0%

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (141607-25-2) + Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidine methyl ester (160054-29-5,170375-01-6) → erythro-Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-09-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; for 2h;

Reference yield: 24.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidine methyl ester (160054-29-5,170375-01-6) → erythro-Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-09-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; for 0.75h;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → erythro-Nα-((benzyloxy)carbonyl)-Nim-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester (170375-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / NaH / CH₂Cl₂ / 0.25 h / 25 °C

2: 24 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 0.75 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; In diethyl ether; dichloromethane;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

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

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

Downstream raw materials:

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

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

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

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