benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

Base Information

Chemical Name:benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside
CAS No.:504422-41-7
Molecular Formula:C₂₃H₂₇NO₅
Molecular Weight:397.471
Hs Code.:

Synonyms:benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

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Chemical Property of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

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Technology Process of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

There total 8 articles about benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-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: 41.0%

: 100-39-0
benzyl bromide

: 504422-40-6
2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranose

: 504422-43-9
2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranose

: 504422-41-7
benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

: benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;
DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 504422-41-7
benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.5 g / p-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

2.1: NaIO₄; NaHCO₃ / H₂O / 5 h / 20 °C

2.2: 56 percent / nitromethane; NaOMe / methanol / 12 h / 20 °C

3.1: H₂ / Raney nickel T-4 / methanol / 40 h / 20 °C / 1875.15 Torr

3.2: 67 percent / pyridine / 20 °C

4.1: 100 percent / NaOMe / methanol / 20 °C

5.1: 3 percent / NaH / dimethylformamide / 1.5 h / 0 °C

With sodium periodate; hydrogen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; Raney nickel T-4; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

: 86117-82-0
(1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol

: 504422-41-7
benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.5 g / p-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

2.1: NaIO₄; NaHCO₃ / H₂O / 5 h / 20 °C

2.2: 56 percent / nitromethane; NaOMe / methanol / 12 h / 20 °C

3.1: H₂ / Raney nickel T-4 / methanol / 40 h / 20 °C / 1875.15 Torr

3.2: 67 percent / pyridine / 20 °C

4.1: 100 percent / NaOMe / methanol / 20 °C

5.1: 3 percent / NaH / dimethylformamide / 1.5 h / 0 °C

With sodium periodate; hydrogen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; Raney nickel T-4; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00294-X