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

Base Information

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-heptadecanediol
CAS No.:1314766-50-1
Molecular Formula:C₆₆H₁₁₆N₂O₁₂
Molecular Weight:1129.65
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-heptadecanediol

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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-heptadecanediol

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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-heptadecanediol

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-heptadecanediol 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:

: C₆₆H₁₁₄N₂O₁₂

: 1314766-50-1
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-heptadecanediol

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

: 1314766-50-1
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-heptadecanediol

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

: 1314766-50-1
(2S,3R)-5-aza-3-O-benzyl-2-heptadecanoylamino-1-O-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-1,3-heptadecanediol

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