(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

Base Information

Chemical Name:(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene
CAS No.:194299-23-5
Molecular Formula:C₅₅H₉₃NO₁₀
Molecular Weight:928.344
Hs Code.:

Synonyms:(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

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Chemical Property of (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

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Technology Process of (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

There total 7 articles about (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene 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: 73.0%

: 3282-30-2
pivaloyl chloride

: 172340-63-5
(2S,3R,4E)-2-hexadecanoylamino-3-benzoyloxy-1-(3,4-O-isopropylidene-β-D-galactopyranosyloxy)-4-octadecene

: 194299-23-5
(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

Guidance literature:: With dmap; at 22 ℃;
DOI:10.1021/jm9606960

Reference yield:

: 103348-50-1
(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

: 194299-23-5
(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / SnCl₄, 4 Angstroem molecular sieves / CH₂Cl₂; hexane / 1 h

2: 89 percent / NaOMe / CH₂Cl₂; methanol / 3 h / -70 - -50 °C

3: H₂S, pyridine / H₂O / 18 h / 22 °C

4: NaOAc, water / tetrahydrofuran

5: 90 percent / p-toluenesulfonic acid / 18 h / 22 °C

6: 73 percent / 4-(dimethylamino)pyridine / 22 °C

With pyridine; dmap; 4 A molecular sieve; hydrogen sulfide; water; sodium methylate; sodium acetate; tin(IV) chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1021/jm9606960

Reference yield:

: 86520-63-0
2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

: 194299-23-5
(2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / SnCl₄, 4 Angstroem molecular sieves / CH₂Cl₂; hexane / 1 h

2: 89 percent / NaOMe / CH₂Cl₂; methanol / 3 h / -70 - -50 °C

3: H₂S, pyridine / H₂O / 18 h / 22 °C

4: NaOAc, water / tetrahydrofuran

5: 90 percent / p-toluenesulfonic acid / 18 h / 22 °C

6: 73 percent / 4-(dimethylamino)pyridine / 22 °C

With pyridine; dmap; 4 A molecular sieve; hydrogen sulfide; water; sodium methylate; sodium acetate; tin(IV) chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1021/jm9606960