6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

Base Information

Chemical Name:6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate
CAS No.:503181-16-6
Molecular Formula:C₂₇H₂₈Cl₆N₂O₈
Molecular Weight:721.246
Hs Code.:

Synonyms:6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

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Chemical Property of 6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

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Technology Process of 6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

There total 4 articles about 6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate 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:

: 545-06-2
trichloroacetonitrile

: 6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

: 503181-16-6
6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

: 503180-90-3
4-pentenyl 2-amino-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

: 503181-16-6
6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / aq. NaHCO₃ / diethyl ether / 1 h

2: 92 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

3: NBS; H₂O / acetonitrile / 14 h

4: 922 mg / DBU / CH₂Cl₂ / 2 h / 0 °C

With dmap; N-Bromosuccinimide; water; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

: 503181-12-2
4-pentenyl 3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 503181-16-6
6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetamidate

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

2: NBS; H₂O / acetonitrile / 14 h

3: 922 mg / DBU / CH₂Cl₂ / 2 h / 0 °C

With dmap; N-Bromosuccinimide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; dichloromethane; acetonitrile;
DOI:10.1016/S0008-6215(02)00299-9