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

Base Information

Chemical Name:(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyloxy)butane
CAS No.:956038-80-5
Molecular Formula:C₄₅H₆₅N₃O₁₃
Molecular Weight:856.023
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

There total 8 articles about (2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-pivaloyl-β-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: 70.0%

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

: C₂₈H₄₄O₁₀NCl₃

: 956038-80-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyloxy)butane

Guidance literature:: With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -50 ℃; for 2.5h;
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

: 956038-80-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyloxy)butane

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / BH₃*THF / tetrahydrofuran / 5 h / Heating

2: 7.49 g / pyridine / 20 °C

3: pyridine / 24 h / 20 °C

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

5: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

6: 70 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -50 °C

With pyridine; sodium azide; borane-THF; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070849z

Reference yield:

: 956038-68-9
(2R,3R)-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,3,4-tetrol

: 956038-80-5
(2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyloxy)butane

Guidance literature:: Multi-step reaction with 5 steps

1: 7.49 g / pyridine / 20 °C

2: pyridine / 24 h / 20 °C

3: 6.30 g / NaN₃ / dimethylformamide / 4 h / 85 °C

4: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5: 70 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -50 °C

With pyridine; sodium azide; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070849z