4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate
CAS No.:150969-32-7
Molecular Formula:C₅₆H₅₆Cl₃NO₁₁
Molecular Weight:1025.42
Hs Code.:

Synonyms:4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

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Technology Process of 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-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: 79.0%

: 545-06-2
trichloroacetonitrile

: (3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-2-ol

: 150969-32-7
4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h;
DOI:10.1016/S0040-4020(01)82378-4

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 150969-32-7
4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1: p-TsOH / dimethylformamide / 2 h / 50 °C

2: NaH / dimethylformamide / 0 °C

3: 1) t-BuOK, 2) HgO, HgCl₂ / 1) DMF, 80 deg C, 2 h, 2) acetone, H₂O, overnight

4: 79 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h

With potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)82378-4

Reference yield:

: 97777-13-4,103136-39-6,50256-34-3
allyl 2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

: 150969-32-7
4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: NaOCH₃ (pH 11) / methanol; CH₂Cl₂

2: p-TsOH / dimethylformamide / 2 h / 50 °C

3: NaH / dimethylformamide / 0 °C

4: 1) t-BuOK, 2) HgO, HgCl₂ / 1) DMF, 80 deg C, 2 h, 2) acetone, H₂O, overnight

5: 79 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h

With potassium tert-butylate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)82378-4