(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

Base Information

Chemical Name:(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal
CAS No.:956038-83-8
Molecular Formula:C₄₅H₄₇N₃O₈
Molecular Weight:757.883
Hs Code.:

Synonyms:(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

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Chemical Property of (2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

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Technology Process of (2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

There total 12 articles about (2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal 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:

: 956038-82-7
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butan-1-ol

: 956038-83-8
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃;
DOI:10.1021/jo070849z

Reference yield:

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

: 956038-83-8
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -50 °C

2: NaOMe / methanol / 20 °C

3: 0.57 g / NaH / dimethylformamide / 24 h

4: 70 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 - 20 °C

5: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

With oxalyl dichloride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1021/jo070849z

Reference yield:

: C₂₈H₄₄O₁₀NCl₃

: 956038-83-8
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)butanal

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -50 °C

2: NaOMe / methanol / 20 °C

3: 0.57 g / NaH / dimethylformamide / 24 h

4: 70 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 - 20 °C

5: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

With oxalyl dichloride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1021/jo070849z