O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Base Information

Chemical Name:O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester
CAS No.:1439931-04-0
Molecular Formula:C₅₁H₅₈N₄O₁₈
Molecular Weight:1015.04
Hs Code.:

O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Synonyms:O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

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Chemical Property of O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

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Technology Process of O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

There total 2 articles about O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline 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: 63.0%

: 1439931-03-9
O-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

: 86520-63-0
2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

: 1439931-04-0
O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Guidance literature:: O-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester; 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -20 ℃; for 1h;
DOI:10.1016/j.bmc.2013.02.025

Reference yield:

: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-trans-L-hydroxyproline tert-butyl ester

: 1439931-04-0
O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-[1'→3]-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 5 h / 20 °C / pH 8 - 8.5

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 16 h / 50 °C / 90.01 Torr

3.1: 1,2-dichloro-ethane / 0.5 h / 20 °C / Molecular sieve

3.2: 1 h / -20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2013.02.025