N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester
• CAS No.: 195976-15-9
• Molecular Formula: C₅₉H₆₀Cl₃N₅O₁₈
• Molecular Weight: 1233.51

Synonyms:N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester

Chemical Property:

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Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester

There total 4 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl 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: 82.0%

Nα-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester (195976-15-9)

Guidance literature:

With acetic acid; at 80 ℃; for 1h;

DOI:10.1039/a701742a

Reference yield:

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester (120791-77-7) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester (195976-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe / methanol / 1 h

2: 65 percent / p-TsOH / nitromethane / 1 h / Ambient temperature

3: 82 percent / MS 4A, TMSOTf / 1,2-dichloro-ethane / 0 °C / 1.) 1 h, 2.) 45 min

4: 82 percent / aq. AcOH / 1 h / 80 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; acetic acid; In methanol; nitromethane; 1,2-dichloro-ethane;

DOI:10.1039/a701742a

Reference yield:

(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester (195976-26-2) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester (195976-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / p-TsOH / nitromethane / 1 h / Ambient temperature

2: 82 percent / MS 4A, TMSOTf / 1,2-dichloro-ethane / 0 °C / 1.) 1 h, 2.) 45 min

3: 82 percent / aq. AcOH / 1 h / 80 °C

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; In nitromethane; 1,2-dichloro-ethane;

DOI:10.1039/a701742a

upstream raw materials:

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester

(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester

N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester

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