2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Base Information

Chemical Name:2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
CAS No.:118638-73-6
Molecular Formula:C₃₂H₅₃NO₈
Molecular Weight:579.775
Hs Code.:

Synonyms:2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Chemical Property of 2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Technology Process of 2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

There total 6 articles about 2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 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: 76.0%

: 118638-72-5
2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-α-D-glucopyranoside

: 77-76-9
2,2-dimethoxy-propane

: 118638-73-6
2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 5h; Ambient temperature;
DOI:10.1248/cpb.38.3366

Reference yield:

: 172490-46-9
2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 118638-73-6
2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1) 5 M HCl, 2) pyridine / 1) dioxane, 90 deg C, 4 h, 2) room temperature, 16 h

2: AcOH, Zn / 1 h / Ambient temperature

3: 1) DCC, HOBt, 2) N-methylmorpholine / 1) THF, 3 h, room temperature, 2) 3 h, room temperature

4: 89 percent / MeONa / methanol / 0.33 h / Ambient temperature

5: 76 percent / p-TsOH*H₂O / dimethylformamide / 5 h / Ambient temperature

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium methylate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; zinc; In methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.38.3366

Reference yield:

: 118638-66-7
2-acetoxyethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 118638-73-6
2-hydroxyethyl 2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: AcOH, Zn / 1 h / Ambient temperature

2: 1) DCC, HOBt, 2) N-methylmorpholine / 1) THF, 3 h, room temperature, 2) 3 h, room temperature

3: 89 percent / MeONa / methanol / 0.33 h / Ambient temperature

4: 76 percent / p-TsOH*H₂O / dimethylformamide / 5 h / Ambient temperature

With 4-methyl-morpholine; sodium methylate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; zinc; In methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.38.3366