(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

Base Information

Chemical Name:(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol
CAS No.:956038-73-6
Molecular Formula:C₅₁H₅₇N₃O₈
Molecular Weight:840.029
Hs Code.:

Synonyms:(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

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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,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

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Technology Process of (2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

There total 11 articles about (2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-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: 75.0%

: 947747-43-5
(2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butanal

: 7154-75-8
4-methylpentyne

: 956038-73-6
(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

Guidance literature:: With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene;
DOI:10.1021/jo070849z

Reference yield:

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

: 956038-73-6
(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

Guidance literature:: Multi-step reaction with 2 steps

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

2: 75 percent / (-)-N-methylephedrine; triethylamine; zinc trifluoromethanesulfonate / toluene

With oxalyl dichloride; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1: Swern oxidation / 2: Carreira reaction;
DOI:10.1021/jo070849z

Reference yield:

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

: 956038-73-6
(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 - 20 °C

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

3: 75 percent / (-)-N-methylephedrine; triethylamine; zinc trifluoromethanesulfonate / toluene

With oxalyl dichloride; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene; 2: Swern oxidation / 3: Carreira reaction;
DOI:10.1021/jo070849z