2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

Base Information

Chemical Name:2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside
CAS No.:500358-95-2
Molecular Formula:C₆₇H₁₀₁N₂O₁₃P
Molecular Weight:1173.52
Hs Code.:

2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

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Chemical Property of 2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

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Technology Process of 2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

There total 17 articles about 2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside 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:

: 500358-94-1
2-(benzyloxymethyl)-3-hydroxy-2-[(2,2,2-trichloroethoxycarbonyl)aminomethyl]-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 500358-95-2
2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

Guidance literature:: With acetic acid; zinc; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(02)01067-0

Reference yield:

: 87357-76-4
(R)-3-(dodecanoyloxy)tetradecanoic acid

: 500358-95-2
2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / N,N'-dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

2.1: 85 percent / NaBH₃CN; HCl; molecular sieves 4 Angstroem / diethyl ether; tetrahydrofuran / 0 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 1.33 g / m-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

5.1: (MePh₂P)2(1,5-cyclooctadiene)Ir(I) hexafluorophosphate; H₂ / tetrahydrofuran / 2 h / 20 °C

5.2: 76 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 1 h / 20 °C

6.1: 76 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

7.1: 81 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

8.1: zinc; acetic acid / 1 h / 20 °C

With 1H-tetrazole; hydrogenchloride; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium cyanoborohydride; caesium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(02)01067-0

Reference yield:

: 130147-42-1
2-<(benzyloxy)methyl>-2-(hydroxymethyl)-1,3-propanediol

: 500358-95-2
2-(benzyloxymethyl)-3-hydroxy-2-(aminomethyl)-prop-1-yl 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-amino-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / p-toluenesulfonic acid / acetonitrile / 1 h / 20 °C

2: 98 percent / pyridine / 3 h / 0 °C

3: 70 percent / NaN₃; NaHCO₃; aliquat / toluene; H₂O / 40 h / Heating

4: zinc; acetic acid / 1 h / 20 °C

5: 28 mg / NaHCO₃ / H₂O; dioxane / 6 h / 20 °C

6: 90 percent / acetic acid / H₂O / 0.75 h / 60 °C

7: 81 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

8: zinc; acetic acid / 1 h / 20 °C

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Aliquat; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; zinc; In 1,4-dioxane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)01067-0