O-(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-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester
CAS No.:1439931-03-9
Molecular Formula:C₃₇H₄₀N₄O₉
Molecular Weight:684.746
Hs Code.:

Synonyms:O-(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-(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-(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-(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:

: 1125-88-8
benzaldehyde dimethyl acetal

: C₃₀H₃₆N₄O₉

: 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

: 1450791-73-7
O-(2-azido-4O,6O-benzylidene-2-deoxy-β-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃; for 16h; under 90.009 Torr;
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

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

: 1450791-73-7
O-(2-azido-4O,6O-benzylidene-2-deoxy-β-D-galactopyranosyl)-N-[(9H-fluoren-9-yl)-methoxycarbonyl]-(4R)-L-hydroxyproline tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

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