Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside
• CAS No.: 161822-70-4
• Molecular Formula: C₃₅H₃₇NO₅Se
• Molecular Weight: 630.642

Synonyms:Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside

Chemical Property of Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside

Chemical Property:

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Technology Process of Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside

There total 2 articles about Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-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:

Phenyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-seleno-α-D-glucopyranoside (150809-70-4) → Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside (161822-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-propanedithiol, Et₃N, NaBH₄ / propan-2-ol / 4 h / 45 °C

2: pyridine

With pyridine; 1.3-propanedithiol; sodium tetrahydroborate; triethylamine; In isopropyl alcohol;

DOI:10.1080/07328309608005438

Reference yield:

acetic anhydride (108-24-7) + (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylselanyl-tetrahydro-pyran-3-ylamine → Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside (161822-70-4)

Guidance literature:

With pyridine; Yield given;

DOI:10.1080/07328309608005438

Reference yield: 88.0%

Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside (161822-70-4) → N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6)

Guidance literature:

With mercury(II) trifluoroacetate; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1080/07328309608005438

upstream raw materials:

acetic anhydride

Phenyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-seleno-α-D-glucopyranoside

Downstream raw materials:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton

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