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

Base Information

Chemical Name:(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butan-1-ol
CAS No.:947747-16-2
Molecular Formula:C₄₅H₄₉N₃O₈
Molecular Weight:759.899
Hs Code.:

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

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

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

There total 18 articles about (2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butan-1-ol 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: 81.0%

: 947747-22-0
C₅₆H₅₇N₃O₈

: 947747-16-2
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butan-1-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane;
DOI:10.1016/j.tetlet.2007.05.161

Reference yield: 70.0%

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

: 947747-16-2
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butan-1-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo070849z

Reference yield:

: 58383-35-0
(R,R)-trans-bis(hydroxymethyl)-1,4-dioxa-5 phenylpentane

: 947747-16-2
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 60 percent / NaH / dimethylformamide / -20 - 0 °C

2.1: 75 percent / BH₃*THF / tetrahydrofuran / 5 h / Heating

3.1: 7.49 g / pyridine / 20 °C

4.1: pyridine / 24 h / 20 °C

5.1: 6.30 g / NaN₃ / dimethylformamide / 4 h / 85 °C

6.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

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

7.2: 85 percent / tetramethylurea; tetrabutylammonium bromide / CH₂Cl₂ / 192 h / 20 °C

8.1: 70 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 - 20 °C

With pyridine; sodium azide; borane-THF; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo070849z