dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

Base Information

Chemical Name:dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate
CAS No.:906545-86-6
Molecular Formula:C₄₆H₅₈NO₁₁P
Molecular Weight:831.94
Hs Code.:

Synonyms:dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

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Chemical Property of dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

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Technology Process of dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

There total 9 articles about dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate 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: 80.0%

: 144634-18-4
methyl (2S)-2-(tert-butoxycarbonylamino)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate

: 756-79-6
dimethyl methane phosphonate

: 906545-86-6
dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

Guidance literature:: dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

methyl (2S)-2-(tert-butoxycarbonylamino)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ol061100y

Reference yield:

: 906545-77-5
(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid

: 906545-86-6
dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2.1: 1.60 g / diethyl ether / 0 °C

3.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

4.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

5.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

6.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

7.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

With pyridine; dmap; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; 1.1: <2,3>-Wittig sigmatropic rearrangement / 4.1: Mitsunobu reaction;
DOI:10.1021/ol061100y

Reference yield:

: 906545-78-6
(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

: 906545-86-6
dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

2.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

3.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

4.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

5.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

With pyridine; dmap; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; triphenylphosphine; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;
DOI:10.1021/ol061100y