N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

Base Information

Chemical Name:N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester
CAS No.:263010-76-0
Molecular Formula:C₄₂H₆₄Cl₃N₃O₁₃
Molecular Weight:925.341
Hs Code.:

N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

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Chemical Property of N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

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Technology Process of N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

There total 7 articles about N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine 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: 36.0%

: N-tetradecanoyl-L-serine benzyl ester

: 263010-75-9
phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 263010-76-0
N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

Guidance literature:: With N-Bromosuccinimide; iodine; tetrabutylammonium trifluoromethylsulfonate; In dichloromethane;
DOI:10.1248/cpb.48.32

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 263010-76-0
N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 47 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 40 - 50 °C

2: 36 percent / NBS; I₂; TBAOTf / CH₂Cl₂

With N-Bromosuccinimide; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; platinum(IV) oxide; In dichloromethane; ethyl acetate; 1: Reduction / 2: glycosidation;
DOI:10.1248/cpb.48.32

Reference yield:

: 172490-46-9
2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 263010-76-0
N-tetradecanoyl-O-[3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 13.5 g / pyridine / 5 h / 20 °C

3: 61 percent / NaN₃; 18-crown-6 / dimethylformamide / 40 h / 40 - 50 °C

4: 61 percent / BF₃*OEt / CH₂Cl₂ / 24 h / 20 °C

5: 47 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 40 - 50 °C

6: 36 percent / NBS; I₂; TBAOTf / CH₂Cl₂

With pyridine; N-Bromosuccinimide; sodium azide; 18-crown-6 ether; boron trifluoride diethyl etherate; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; platinum(IV) oxide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: tosylation / 2: Acetylation / 3: Substitution / 4: thioglycosidation / 5: Reduction / 6: glycosidation;
DOI:10.1248/cpb.48.32