methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Base Information

Chemical Name:methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside
CAS No.:496065-71-5
Molecular Formula:C₃₆H₄₃NO₉
Molecular Weight:633.739
Hs Code.:

Synonyms:methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

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Chemical Property of methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

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Technology Process of methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

There total 6 articles about methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside 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: 54.0%

: 496065-70-4
methyl 2-acetamido-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

: phenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-1-thio-α,β-D-ribo-hexopyranoside

: 496065-71-5
methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; for 3h;
DOI:10.1139/v02-117

Reference yield:

: 87038-18-4
methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 496065-71-5
methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

2: 95 percent / NaBH₃CN; molecular sieves 4 Angstroem; hydrogen chloride / methyl orange / tetrahydrofuran; diethyl ether / 2 h

3: 94 percent / toluene / 90 °C

4: 88 percent / tributyltin hydride; azobis(isobutyronitrile) / toluene / 4 h / Heating

5: 94 percent / sodium methoxide / methanol / 2 h / 20 °C

6: 54 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h

With pyridine; hydrogenchloride; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; sodium cyanoborohydride; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 4: Barton-McCombie deoxygenation / 5: Zemplen transesterification;
DOI:10.1139/v02-117

Reference yield:

: 496065-66-8
methyl 2-acetamido-3-O-benzoyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 496065-71-5
methyl 2-acetamido-3-O-(2-O-benzoyl-4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-6-O-benzyl-2,4-dideoxy-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / NaBH₃CN; molecular sieves 4 Angstroem; hydrogen chloride / methyl orange / tetrahydrofuran; diethyl ether / 2 h

2: 94 percent / toluene / 90 °C

3: 88 percent / tributyltin hydride; azobis(isobutyronitrile) / toluene / 4 h / Heating

4: 94 percent / sodium methoxide / methanol / 2 h / 20 °C

5: 54 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h

With hydrogenchloride; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; sodium cyanoborohydride; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 3: Barton-McCombie deoxygenation / 4: Zemplen transesterification;
DOI:10.1139/v02-117