ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

Base Information

Chemical Name:ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate
CAS No.:956038-84-9
Molecular Formula:C₄₉H₅₃N₃O₉
Molecular Weight:827.975
Hs Code.:

Synonyms:ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

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Chemical Property of ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

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Technology Process of ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

There total 13 articles about ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate 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: 60.0%

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

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 956038-84-9
ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

Guidance literature:: In toluene; at 20 ℃; for 4h;
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

: 956038-84-9
ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

Guidance literature:: Multi-step reaction with 6 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

6: 60 percent / toluene / 4 h / 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; toluene; 5: Swern oxidation / 6: Wittig reaction;
DOI:10.1021/jo070849z

Reference yield:

: C₂₈H₄₄O₁₀NCl₃

: 956038-84-9
ethyl (2E,4R,5S)-5-azido-4-benzyloxy-6-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-2-hexenoate

Guidance literature:: Multi-step reaction with 6 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

6: 60 percent / toluene / 4 h / 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; toluene; 5: Swern oxidation / 6: Wittig reaction;
DOI:10.1021/jo070849z