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

Base Information

Chemical Name: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
CAS No.:500358-94-1
Molecular Formula:C₇₃H₁₀₃Cl₆N₂O₁₇P
Molecular Weight:1524.32
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 15 articles about 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 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: 81.0%

: 500358-93-0
2-(benzyloxymethyl)-2-(2,2,2-trichloroethoxycarbonylaminomethyl)-1,3-propanediol

: 6-O-benzyl-2-deoxy-4-O-(di-O-benzyl-phosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

: 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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(02)01067-0

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With 1H-tetrazole; hydrogenchloride; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium cyanoborohydride; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 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

: 500358-94-1
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

Guidance literature:: Multi-step reaction with 7 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

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