N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

Base Information

Chemical Name:N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester
CAS No.:188583-12-2
Molecular Formula:C₄₀H₅₉Cl₃N₂O₁₃
Molecular Weight:882.273
Hs Code.:

Synonyms:N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

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Chemical Property of N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

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Technology Process of N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

There total 4 articles about N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester 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: 64.0%

: 187022-49-7
(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate

: 188583-11-1
N-tetradecanoyl-L-homoserine benzyl ester

: 188583-12-2
N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

Guidance literature:: With N-Bromosuccinimide; 4 A molecular sieve; iodine; tetrabutylammonium trifluoromethylsulfonate; In dichloromethane; at -20 ℃; for 1h;
DOI:10.1248/cpb.45.312

Reference yield:

: 100-39-0
benzyl bromide

: 188583-12-2
N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / NaI / dimethylsulfoxide / 20 h / Ambient temperature

2: 64 percent / 4 A molecular sieves, N-bromosuccinimide, iodine, tetrabutylammonium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

With N-Bromosuccinimide; 4 A molecular sieve; iodine; tetrabutylammonium trifluoromethylsulfonate; sodium iodide; In dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.45.312

Reference yield:

: 122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9
1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 188583-12-2
N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

2: 64 percent / 4 A molecular sieves, N-bromosuccinimide, iodine, tetrabutylammonium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

With N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; iodine; tetrabutylammonium trifluoromethylsulfonate; In dichloromethane;
DOI:10.1248/cpb.45.312