benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Base Information

Chemical Name:benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside
CAS No.:484647-53-2
Molecular Formula:C₄₄H₄₇NO₈
Molecular Weight:717.859
Hs Code.:

Synonyms:benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

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Chemical Property of benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

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Technology Process of benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

There total 7 articles about benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside 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: 90.0%

: 484647-52-1
benzyl 3,4,7-tri-O-benzyl-6-(N-methyl-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-L-glycero-α-D-gluco-heptopyranoside

: 484647-53-2
benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 0.5h;
DOI:10.1021/ja028386w

Reference yield:

: 100-39-0
benzyl bromide

: 484647-53-2
benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂SnO / toluene; methanol / 3 h / Heating

1.2: 81 percent / tetrabutylammonium bromide / toluene / 85 °C

2.1: 89 percent / DEAD; PPh₃; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 20 °C

3.1: PPh₃ / H₂O; tetrahydrofuran / 1 h / Heating

4.1: 285.2 mg / TEA / CH₂Cl₂ / 20 °C

5.1: 94 percent / NaH / tetrahydrofuran / 6 h / 20 °C

6.1: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

With TEA; diphenylphosphoranyl azide; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2.1: Bose-modified Mitsunobu reaction;
DOI:10.1021/ja028386w

Reference yield:

: 484647-48-5
benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-gluco-heptopyranoside

: 484647-53-2
benzyl 3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂SnO / toluene; methanol / 3 h / Heating

1.2: 81 percent / tetrabutylammonium bromide / toluene / 85 °C

2.1: 89 percent / DEAD; PPh₃; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 20 °C

3.1: PPh₃ / H₂O; tetrahydrofuran / 1 h / Heating

4.1: 285.2 mg / TEA / CH₂Cl₂ / 20 °C

5.1: 94 percent / NaH / tetrahydrofuran / 6 h / 20 °C

6.1: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

With TEA; diphenylphosphoranyl azide; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2.1: Bose-modified Mitsunobu reaction;
DOI:10.1021/ja028386w