benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

Base Information

Chemical Name:benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside
CAS No.:484647-66-7
Molecular Formula:C₅₁H₅₃NO₉
Molecular Weight:823.983
Hs Code.:

Synonyms:benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

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Chemical Property of benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

Chemical Property:

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Technology Process of benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

There total 7 articles about benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-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:

: 501-53-1,94274-21-2
benzyl chloroformate

: (R)-2-Benzyloxy-1-[(2R,3R,4S,5R,6S)-3,4,6-tris-benzyloxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethylamine

: 484647-66-7
benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

Guidance literature:: With TEA; In dichloromethane; at 20 ℃;
DOI:10.1021/ja028386w

Reference yield:

: benzyl 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-(L/D)-glycero-α-D-glucoheptopyranoside

: 484647-66-7
benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / DEAD; PPh₃ / tetrahydrofuran / 5 h / 20 °C

2: 96 percent / K₂CO₃ / methanol / 2 h / 20 °C

3: 89 percent / DEAD; PPh₃; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 20 °C

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

5: TEA / CH₂Cl₂ / 20 °C

With TEA; diphenylphosphoranyl azide; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1: Mitsunobu reaction / 3: Bose-modified Mitsunobu reaction;
DOI:10.1021/ja028386w

Reference yield:

: 100-39-0
benzyl bromide

: 484647-66-7
benzyl 3,4,7-tri-O-benzyl-6-(N-benzyloxycarbonylamino)-6-deoxy-2-O-(p-methoxybenzyl)-D-glycero-α-D-gluco-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 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: TEA / CH₂Cl₂ / 20 °C

With TEA; diphenylphosphoranyl azide; di(n-butyl)tin oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2.1: Bose-modified Mitsunobu reaction;
DOI:10.1021/ja028386w