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

Base Information

Chemical Name: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
CAS No.:120791-77-7
Molecular Formula:C₃₅H₄₂N₄O₁₂
Molecular Weight:710.738
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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:

: 73731-37-0
Fmoc-Thr-OH

: 120791-77-7
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

Guidance literature:: Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide; copper(l) chloride

2: silver (II) carbonate; silver perchlorate

With silver (II) carbonate; silver perchlorate; dicyclohexyl-carbodiimide; copper(l) chloride; 2: Koenigs-Knorr synthesis;
DOI:10.1002/ejoc.201100304

Reference yield: 53.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 120791-77-7
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

: C₃₈H₄₂N₄O₁₀

Guidance literature:: 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; With sodium methylate; In methanol; at 20 ℃; for 3h; Inert atmosphere;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In nitromethane; for 2h; Inert atmosphere;
DOI:10.1016/j.carres.2010.05.004

Reference yield:

: 120791-77-7
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

: N-(9H-fluorene-9-yl)-methoxycarbonyl-O-{2-difluoroacetamido-3,4-di-O-acetyl-2-deoxy-6-O-[benzyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-galactopyranosyl}-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: zinc; acetic acid / 3 h / 20 °C

2.1: sodium hydrogencarbonate / acetonitrile / 0.17 h

3.1: sodium methylate / methanol / 0.5 h / pH < 9

3.2: Dowex^?50WX4 ion-exchange resin (H⁺) / 0.5 h

4.1: methylsulfenyl bromide; silver trifluoromethanesulfonate / acetonitrile; dichloromethane / 3 h / -62 °C / Molecular sieve; Inert atmosphere

5.1: pyridine / 12 h

With pyridine; methylsulfenyl bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydrogencarbonate; acetic acid; zinc; In methanol; dichloromethane; acetonitrile;
DOI:10.1039/c6ob01092j