2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside
CAS No.:286845-73-6
Molecular Formula:C₆₁H₆₂F₃NO₁₅
Molecular Weight:1106.16
Hs Code.:

2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Synonyms:2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of 2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

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Technology Process of 2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

There total 16 articles about 2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside 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: 89.0%

: 286845-72-5
2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-6-O-chloroacetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

: 286845-73-6
2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With hydrazine dithiocarbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

: 20701-63-7
ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 286845-73-6
2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-trimethylamine complex; molecular sieves 4A / CH₂Cl₂; diethyl ether / 1 h

1.2: 84 percent / AlCl₃ / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

2.1: 79 percent / pyridine / CH₂Cl₂ / 1 h / 10 °C

3.1: 95 percent / molecular sieves 4A; NIS; AgOTf / CH₂Cl₂ / 1 h / 0 - 20 °C

4.1: 89 percent / hydrazine dithiocarbonate / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

With pyridine; N-iodo-succinimide; trimethylamine-borane; hydrazine dithiocarbonate; 4 A molecular sieve; silver trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Ring cleavage / 2.1: Acylation / 3.1: Condensation / 4.1: deprotection;
DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

: 7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3
ethyl 1-thio-α-D-mannopyranoside

: 286845-73-6
2-(4-trifluoroacetamidophenyl)ethyl (2,3-di-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine; 4-dimethylaminopyridine

2.1: p-toluenesulfonic acid / dimethylformamide / 2 h / 20 °C

3.1: NaH / dimethylformamide / 1 h / 0 °C

3.2: 80 percent / dimethylformamide / 2 h / 0 °C

4.1: 62 percent / aq. formic acid / ethyl acetate / 2.5 h

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

6.1: 31 percent / Mg; HgBr₂ / tetrahydrofuran / 10 - 20 °C

7.1: NaH / light petroleum; dimethylformamide / 2 h

7.2: 82 percent / light petroleum; dimethylformamide / 2 h / 20 °C

8.1: 60 percent / molecular sieves 4A; NIS; AgOTf / CH₂Cl₂; acetonitrile / 1.5 h / 20 °C

9.1: 80 percent / aq. DDQ / CH₂Cl₂ / 2 h

10.1: 95 percent / molecular sieves 4A; NIS; AgOTf / CH₂Cl₂ / 1 h / 0 - 20 °C

11.1: 89 percent / hydrazine dithiocarbonate / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; formic acid; oxalyl dichloride; hydrazine dithiocarbonate; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dibromide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Petroleum ether; 1.1: Alkylation / 2.1: acetalization / 3.1: Metallation / 3.2: Substitution / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: Metallation / 7.2: Substitution / 8.1: Substitution / 9.1: deprotection / 10.1: Condensation / 11.1: deprotection;
DOI:10.1016/S0957-4166(99)00554-6