octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 1344088-78-3
• Molecular Formula: C₂₈H₃₇N₃O₄S
• Molecular Weight: 511.685

Synonyms:octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

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Technology Process of octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

There total 6 articles about octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-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: 89.0%

octyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside (1344088-77-2) + benzyl bromide (100-39-0) → octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside (1344088-78-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.carres.2011.08.001

Reference yield:

octyl 2-azido-2-deoxy-1-thio-α-D-glucopyranoside (1344088-76-1) → octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside (1344088-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid / acetonitrile / 3 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

With sodium hydride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2011.08.001

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → octyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside (1344088-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid / acetonitrile / 3 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

With sodium hydride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2011.08.001

upstream raw materials:

octyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

benzyl bromide

octyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-glucopyranoside

octyl 2-azido-2-deoxy-1-thio-α-D-glucopyranoside

Downstream raw materials:

octyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

octyl 3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

octyl 3-O-acetyl-2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

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