N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

Base Information

Chemical Name:N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester
CAS No.:683773-06-0
Molecular Formula:C₄₅H₄₈Cl₄N₂O₁₁
Molecular Weight:934.695
Hs Code.:

N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

Synonyms:N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

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Chemical Property of N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

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Technology Process of N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

There total 14 articles about N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine 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%

: 516-12-1
N-iodo-succinimide

: 683773-00-4
4-pentenyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranoside

: 683773-05-9
N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl-D-allothreonine benzyl ester

: 4-iodo-5-(N-succinimidyl)pentyl 3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranoside

: 683773-06-0
N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1021/jo030304e

Reference yield:

: 176505-52-5
(2R,3R)-2-Azido-3-hydroxy-butyric acid benzyl ester

: 683773-06-0
N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / hydrogen; aq. HCl / Pt/C / dioxane / normal pressure

2: 79 percent / IIDQ / CH₂Cl₂

3: 64 percent / TMS triflate / CH₂Cl₂ / 0.25 h / 20 °C

With hydrogenchloride; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; trimethylsilyl trifluoromethanesulfonate; hydrogen; platinum on activated charcoal; In 1,4-dioxane; dichloromethane;
DOI:10.1021/jo030304e

Reference yield:

: 3615-41-6,478518-52-4
L-Rhamnose

: 683773-06-0
N-[N-[(2,2,2-trichloroethoxy)carbonyl]-D-phenylalaninyl]-O-(3,4-di-O-benzyl-2-O-chloroacetyl-6-deoxy-α-L-talopyranosyl)-D-allothreonine benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: p-toluenesulfonic acid monohydrate / 36 h / 95 °C

2.1: 2.1 g / CH₂Cl₂ / 24 h / 20 °C

3.1: 88 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

4.1: 93 percent / sodium borohydride / aq. ethanol / 2 h / 20 °C

5.1: NaOH / dioxane / 80 °C

6.1: 3.5 g / aq. AcOH / 1 h / 50 °C

7.1: Bu₂SnO / benzene / 24 h / Heating

7.2: 41 percent / Bu₄NBr / benzene / 24 h / Heating

8.1: 91 percent / pyridine / CH₂Cl₂ / cooling

9.1: 64 percent / TMS triflate / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In 1,4-dioxane; ethanol; dichloromethane; benzene;
DOI:10.1021/jo030304e