2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Base Information

Chemical Name:2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
CAS No.:288402-91-5
Molecular Formula:C₃₂H₄₉Cl₃N₄O₆
Molecular Weight:692.123
Hs Code.:

Synonyms:2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Chemical Property of 2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Technology Process of 2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

There total 10 articles about 2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 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: 88.0%

: ammonium chloride

: 6674-22-2,83329-50-4
1,8-diazabicyclo[5.4.0]undec-7-ene

: 545-06-2
trichloroacetonitrile

: 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-D-glucopyranose

: 288402-91-5
2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: In dichloromethane;

Reference yield: 88.0%

: 545-06-2
trichloroacetonitrile

: 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-D-glucopyranose

: 288402-91-5
2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 288402-91-5
2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / pTsOH*H₂O / dimethylformamide / 1 h / 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

3.1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C

5.1: [C₈H₁₂Ir(PMePh₂)2]PF₆; H₂ / tetrahydrofuran / 3 h / 20 °C

5.2: 65 percent / I₂; water; pyridine / 12 h / 20 °C

6.1: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With [C₈H₁₂Ir(PMePh₂)2]PF₆; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6