2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:1622317-93-4
Molecular Formula:C₅₅H₅₈N₂O₁₆
Molecular Weight:1003.07
Hs Code.:

Synonyms:2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about 2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-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: 73.0%

: 1622317-90-1
2-(benzyloxycarbonylamino)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: O-(4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)trichloroacetimidate

: 1622317-93-4
2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With nitrosonium tetrafluoroborate; In diethyl ether; dichloromethane; at -10 ℃; for 0.5h; stereospecific reaction; Inert atmosphere;
DOI:10.1002/ejoc.201402392

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 1622317-93-4
2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 16 h / 55 °C

2: sodium methylate / methanol / 1 h / 20 °C

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C

4: triethylsilane; iodine / acetonitrile / 0.5 h / 5 °C

5: nitrosonium tetrafluoroborate / dichloromethane; diethyl ether / 0.5 h / -10 °C / Inert atmosphere

With triethylsilane; boron trifluoride diethyl etherate; iodine; sodium methylate; nitrosonium tetrafluoroborate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201402392

Reference yield:

: 77987-49-6
benzyl 2-hydroxyethylcarbamate

: 1622317-93-4
2-(benzyloxycarbonylamino)ethyl (4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 16 h / 55 °C

2: sodium methylate / methanol / 1 h / 20 °C

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C

4: triethylsilane; iodine / acetonitrile / 0.5 h / 5 °C

5: nitrosonium tetrafluoroborate / dichloromethane; diethyl ether / 0.5 h / -10 °C / Inert atmosphere

With triethylsilane; boron trifluoride diethyl etherate; iodine; sodium methylate; nitrosonium tetrafluoroborate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201402392