(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

Base Information

Chemical Name:(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol
CAS No.:130259-21-1
Molecular Formula:C₇₄H₁₃₁N₅O₁₃
Molecular Weight:1298.88
Hs Code.:

(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

Synonyms:(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

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Chemical Property of (2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

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Technology Process of (2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

There total 7 articles about (2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-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: 95.0%

: 130259-20-0
(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-4,6-O-isopropylidene-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

: 130259-21-1
(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 2h;
DOI:10.1016/0008-6215(90)84080-E

Reference yield:

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

: 130259-21-1
(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1. 4 Angstroem molecular sieves 2. BF₃*Et₂O / 1. ether, 3 h, room temperature 2. 24 h

2: 86 percent / M KOH, H₂O / dioxane / 48 h / Ambient temperature

3: 1. N-hydroxysuccinimide, dicyclohexylcarbodi-imide 2. NEt₃ / 1. THF, 45 min, room temperature 2. 20 h, room temperature

4: H₂S / pyridine; H₂O / 24 h

5: 61 percent / 50percent aq. sodium acetate / tetrahydrofuran / 1 h

6: 95 percent / 60percent aq. trifluoroacetic acid / CH₂Cl₂ / 2 h

With potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; 4 A molecular sieve; hydrogen sulfide; water; sodium acetate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water;
DOI:10.1016/0008-6215(90)84080-E

Reference yield:

: (2S,3R,4E)-2-azido-1-<2-azido-3-O-<(1R)-1-carboxyethyl>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyloxy>-4-octadecen-3-ol

: 130259-21-1
(2S,3R,4E)-1-<2-deoxy-2-hexadecanoylamino-3-O-<(2R)-propanoyl-(L-alanyl-D-isoglutamine benzyl ester)-2-yl>-β-D-glucopyranosyloxy>-2-hexadecanoylamino-4-octadecen-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1. N-hydroxysuccinimide, dicyclohexylcarbodi-imide 2. NEt₃ / 1. THF, 45 min, room temperature 2. 20 h, room temperature

2: H₂S / pyridine; H₂O / 24 h

3: 61 percent / 50percent aq. sodium acetate / tetrahydrofuran / 1 h

4: 95 percent / 60percent aq. trifluoroacetic acid / CH₂Cl₂ / 2 h

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen sulfide; sodium acetate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1016/0008-6215(90)84080-E