(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

Base Information

Chemical Name:(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane
CAS No.:956038-72-5
Molecular Formula:C₅₃H₅₇N₃O₉
Molecular Weight:880.05
Hs Code.:

Synonyms:(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

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Chemical Property of (2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

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Technology Process of (2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

There total 8 articles about (2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane 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: 85.0%

: 956038-71-4
(2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,4-triol

: 6386-24-9
2,3,4,6-tetra-O-benzyl-D-galactopyranose

: 956038-72-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

Guidance literature:: 2,3,4,6-tetra-O-benzyl-D-galactopyranose; With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 3h;

(2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,4-triol; With tetrabutylammomium bromide; tetramethylurea; In dichloromethane; at 20 ℃; for 192h; Further stages.;
DOI:10.1021/jo070849z

Reference yield:

: 956038-67-8
(2R,3R)-2,3-O-benzylidene-1-O-(4-methoxybenzyl)butane-1,2,3,4-tetrol

: 956038-72-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 75 percent / BH₃*THF / tetrahydrofuran / 5 h / Heating

2.1: 7.49 g / pyridine / 20 °C

3.1: pyridine / 24 h / 20 °C

4.1: 6.30 g / NaN₃ / dimethylformamide / 4 h / 85 °C

5.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

6.1: PPh₃; CBr₄ / CH₂Cl₂ / 3 h / 20 °C

6.2: 85 percent / tetramethylurea; tetrabutylammonium bromide / CH₂Cl₂ / 192 h / 20 °C

With pyridine; sodium azide; borane-THF; carbon tetrabromide; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070849z

Reference yield:

: 956038-69-0
(2R,3R)-3-O-benzyl-4-O-(4-methoxybenzyl)-1-O-(thexyldimethylsilyl)butane-1,2,3,4-tetrol

: 956038-72-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / 24 h / 20 °C

2.1: 6.30 g / NaN₃ / dimethylformamide / 4 h / 85 °C

3.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: PPh₃; CBr₄ / CH₂Cl₂ / 3 h / 20 °C

4.2: 85 percent / tetramethylurea; tetrabutylammonium bromide / CH₂Cl₂ / 192 h / 20 °C

With pyridine; sodium azide; carbon tetrabromide; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070849z