(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

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Chemical Name:(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol
CAS No.:1314766-52-3
Molecular Formula:C₅₉H₁₀₂N₂O₁₂
Molecular Weight:1031.47
Hs Code.:

Synonyms:(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

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Chemical Property of (2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

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Technology Process of (2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

There total 10 articles about (2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol 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:

: C₅₉H₁₀₀N₂O₁₂

: 1314766-52-3
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

Guidance literature:: With sodium cyanoborohydride; In methanol; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2011.05.054

Reference yield:

: 1314766-43-2
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-3-(thiazol-2-yl)-1,3-propanediol

: 1314766-52-3
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

Guidance literature:: Multi-step reaction with 7 steps

1.1: dichloromethane / 1 h / Molecular sieve; Inert atmosphere

1.2: 3 h / -15 °C / Inert atmosphere; Molecular sieve

2.1: trifluoroacetic acid / dichloromethane / 3 h

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4.1: acetonitrile / 12 h / Reflux

5.1: sodium tetrahydroborate / methanol / 0.58 h / 0 - 20 °C

5.2: 1 h / 20 °C

6.1: methanol / 2 h / 20 °C

7.1: sodium cyanoborohydride / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.05.054

Reference yield:

: 1314766-44-3
(2S,3S)-3-O-benzyl-2-tert-butyloxycarbonylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-3-(thiazol-2-yl)-1,3-propanediol

: 1314766-52-3
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-decanediol

Guidance literature:: Multi-step reaction with 6 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: acetonitrile / 12 h / Reflux

4.1: sodium tetrahydroborate / methanol / 0.58 h / 0 - 20 °C

4.2: 1 h / 20 °C

5.1: methanol / 2 h / 20 °C

6.1: sodium cyanoborohydride / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.05.054