N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

Base Information

Chemical Name:N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide
CAS No.:77594-18-4
Molecular Formula:C₂₉H₄₃N₃O₉
Molecular Weight:577.675
Hs Code.:

N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

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Chemical Property of N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

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Technology Process of N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

There total 25 articles about N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide 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:

: 64552-06-3
methyl 4,6-O-benzylidene-α-D-galactopyranoside

: 77594-18-4
N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaH / 1.) DMF, 1.5 h, 20 deg C, 2.) 3 h, 20 deg C

2: 80 percent AcOH aq. / 3 h / 80 - 85 °C

3: pyridine / 20 h / 20 °C

4: 91 percent / pyridine / 1.) -5 - 0 deg C, 10 min, 2.) 17 h, 20 deg C

5: 93.4 percent / sodium azide / dimethylformamide / 25 h / 140 - 160 °C

6: 95 percent / 80 percent AcOH aq. / 3 h / 80 °C

7: 98 percent / pyridine / 15 h / 20 °C

8: 75.5 percent / conc. H₂SO₄ / 0.5 h / 20 °C

9: 22.4 percent / HCl / CH₂Cl₂ / 1.) -5 deg C, 2.) 20 deg C, 15 h

10: 1.) Et₄NCl, Et(i-Pr)2N, 2) 80 percent AcOH aq. / 1.) ClCH₂ClCH₂, reflux, 3 d, 2.) 20 deg C, 2 d

11: H₂ / Lindlar / ethanol / 6 h / 20 °C

12: AcOH / ethanol / 15 h / 20 °C

With pyridine; hydrogenchloride; sodium azide; sulfuric acid; tetraethylammonium chloride; hydrogen; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(80)80148-7

Reference yield:

: 7177-79-9,13035-24-0,13225-19-9,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9
methyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-α-D-galactopyranoside

: 77594-18-4
N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent AcOH aq. / 3 h / 80 - 85 °C

2: pyridine / 20 h / 20 °C

3: 91 percent / pyridine / 1.) -5 - 0 deg C, 10 min, 2.) 17 h, 20 deg C

4: 93.4 percent / sodium azide / dimethylformamide / 25 h / 140 - 160 °C

5: 95 percent / 80 percent AcOH aq. / 3 h / 80 °C

6: 98 percent / pyridine / 15 h / 20 °C

7: 75.5 percent / conc. H₂SO₄ / 0.5 h / 20 °C

8: 22.4 percent / HCl / CH₂Cl₂ / 1.) -5 deg C, 2.) 20 deg C, 15 h

9: 1.) Et₄NCl, Et(i-Pr)2N, 2) 80 percent AcOH aq. / 1.) ClCH₂ClCH₂, reflux, 3 d, 2.) 20 deg C, 2 d

10: H₂ / Lindlar / ethanol / 6 h / 20 °C

11: AcOH / ethanol / 15 h / 20 °C

With pyridine; hydrogenchloride; sodium azide; sulfuric acid; tetraethylammonium chloride; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(80)80148-7

Reference yield:

: 71756-39-3
methyl 2,3-di-O-benzyl-4-O-mesyl-6-O-trityl-α-D-galactopyranoside

: 77594-18-4
N-[(2S,3R,4S,5R,6R)-6-((1S,2S,3R,4S)-3-Amino-1-aminomethyl-2,4,5-trihydroxy-pentyloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: Multi-step reaction with 8 steps

1: 93.4 percent / sodium azide / dimethylformamide / 25 h / 140 - 160 °C

2: 95 percent / 80 percent AcOH aq. / 3 h / 80 °C

3: 98 percent / pyridine / 15 h / 20 °C

4: 75.5 percent / conc. H₂SO₄ / 0.5 h / 20 °C

5: 22.4 percent / HCl / CH₂Cl₂ / 1.) -5 deg C, 2.) 20 deg C, 15 h

6: 1.) Et₄NCl, Et(i-Pr)2N, 2) 80 percent AcOH aq. / 1.) ClCH₂ClCH₂, reflux, 3 d, 2.) 20 deg C, 2 d

7: H₂ / Lindlar / ethanol / 6 h / 20 °C

8: AcOH / ethanol / 15 h / 20 °C

With pyridine; hydrogenchloride; sodium azide; sulfuric acid; tetraethylammonium chloride; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(80)80148-7