benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine

Base Information

• Chemical Name: benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine
• CAS No.: 217180-17-1
• Molecular Formula: C₆₈H₆₈N₄O₂₄
• Molecular Weight: 1325.3

Synonyms:benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine

Chemical Property of benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine

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Technology Process of benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine

There total 1 articles about benzyl erythro-N^α,N^im-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-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: 58.0%

3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate (162111-91-3) + 4-[(1R,2S)-2-Benzyloxycarbonyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-1-hydroxy-ethyl]-imidazole-1-carboxylic acid 9H-fluoren-9-ylmethyl ester → benzyl erythro-Nα,Nim-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine (217180-17-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/ja9819458

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + benzyl erythro-Nα,Nim-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine (217180-17-1) → C48H64N4O24 (217180-18-2)

Guidance literature:

With piperidine; Yield given. Multistep reaction; 1.) 25 deg C;

DOI:10.1021/ja9819458

Reference yield:

benzyl erythro-Nα,Nim-bis(9-fluorenylmethoxycarbonyl)-β-[3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl]-S-histidine (217180-17-1) → C41H58N4O24 (217180-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) piperidine / 1.) 25 deg C

2: 99 percent / H₂ / 10percent Pd/C

With piperidine; hydrogen; palladium on activated charcoal;

DOI:10.1021/ja9819458

upstream raw materials:

3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate

Downstream raw materials:

C₄₈H₆₄N₄O₂₄

C₄₁H₅₈N₄O₂₄

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