benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

Base Information

Chemical Name:benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate
CAS No.:150631-07-5
Molecular Formula:C₄₀H₄₁Cl₃N₂O₁₄
Molecular Weight:880.13
Hs Code.:

Synonyms:benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

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Chemical Property of benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

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Technology Process of benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

There total 5 articles about benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate 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: 95.0%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: (S)-2-Amino-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-propionic acid benzyl ester

: 150631-07-5
benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/jo005712m

Reference yield: 77.0%

: 118358-66-0,73724-46-6
N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

: Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-6-allylcarbamoyloxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

: 150631-07-5
benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

Guidance literature:: With Methylthio(bismethylthio)sulfonium hexachloroantimonate; In dichloromethane; at -15 - 0 ℃; for 0.75h; molecular sieves;
DOI:10.1016/S0040-4039(00)60478-1

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 150631-07-5
benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

Guidance literature:: Multi-step reaction with 4 steps

1: 34 percent / NaHCO₃ / H₂O / 20 °C

2: 98 percent / pyridine / 12 h / 20 °C

3: 96 percent / HBr / CH₂Cl₂; acetic acid / 0 - 20 °C

4: 66 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / 10 h / 0 °C

With 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; sodium hydrogencarbonate; In pyridine; dichloromethane; water; acetic acid; 4: Koenigs-Knorr reaction;
DOI:10.1021/jo005712m