6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate
CAS No.:828939-52-2
Molecular Formula:C₄₆H₅₉Cl₆N₂O₁₁P
Molecular Weight:1059.67
Hs Code.:

6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

Synonyms:6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

There total 8 articles about 6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate 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: 59.0%

: 545-06-2
trichloroacetonitrile

: 828939-51-1
6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 828939-52-2
6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With caesium carbonate; In dichloromethane; for 1h;
DOI:10.1016/j.tet.2004.10.017

Reference yield:

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 828939-52-2
6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-tetrazole; borane-dimethylamine complex / CH₂Cl₂; acetonitrile / 0.5 h

1.2: 44 percent / tert-butylhydroperoxide / CH₂Cl₂; acetonitrile / 6 h / 0 °C

2.1: {[bis(MePh₂)phosphine](1,5-cyclooctadiene) iridium(I)}PF₆; H₂ / tetrahydrofuran

3.1: 527 mg / iodine / tetrahydrofuran; H₂O / 0 - 25 °C

4.1: 59 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h

With 1H-tetrazole; hydrogen; iodine; caesium carbonate; borane dimethylamine complex; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2004.10.017

Reference yield:

: 112-64-1
tetradecanoyl chloride

: 828939-52-2
6-O-benzyl-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-tetradecanoyl-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / pyridine / tetrahydrofuran / 1 h

2.1: 92 percent / triethylsilane; trifluoromethanesulfonic acid; molecular sieves 0.4 nm / CH₂Cl₂ / 0.67 h / -78 °C

3.1: 1H-tetrazole; borane-dimethylamine complex / CH₂Cl₂; acetonitrile / 0.5 h

3.2: 44 percent / tert-butylhydroperoxide / CH₂Cl₂; acetonitrile / 6 h / 0 °C

4.1: {[bis(MePh₂)phosphine](1,5-cyclooctadiene) iridium(I)}PF₆; H₂ / tetrahydrofuran

5.1: 527 mg / iodine / tetrahydrofuran; H₂O / 0 - 25 °C

6.1: 59 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; iodine; caesium carbonate; borane dimethylamine complex; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2004.10.017