methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

Base Information

Chemical Name:methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate
CAS No.:906545-84-4
Molecular Formula:C₃₉H₄₃N₃O₇
Molecular Weight:665.786
Hs Code.:

Synonyms:methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

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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 methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

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Technology Process of methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

There total 6 articles about methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate 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: 90.0%

: 906545-82-2
methyl (2R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-methylsulfonyloxy-butanoate

: 906545-84-4
methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 85 ℃; for 1h;
DOI:10.1021/ol061100y

Reference yield:

: 906545-78-6
(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

: 906545-84-4
methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

2: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

3: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

With dmap; sodium azide; hydrogen; triphenylphosphine; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 2: Mitsunobu reaction;
DOI:10.1021/ol061100y

Reference yield:

: 906545-77-5
(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid

: 906545-84-4
methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

Guidance literature:: Multi-step reaction with 5 steps

1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2: 1.60 g / diethyl ether / 0 °C

3: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

4: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

5: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

With dmap; sodium azide; hydrogen; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; n-heptane; ethylbenzene; N,N-dimethyl-formamide; 1: <2,3>-Wittig sigmatropic rearrangement / 4: Mitsunobu reaction;
DOI:10.1021/ol061100y