allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Base Information

• Chemical Name: allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside
• CAS No.: 727380-35-0
• Molecular Formula: C₄₅H₅₁N₃O₁₁
• Molecular Weight: 809.913

Synonyms:allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Chemical Property of allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

There total 2 articles about allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside 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%

acetyl chloride (75-36-5) + (2R,3R,4S,5R,6S)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol (628281-09-4) → allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside (727380-35-0)

Guidance literature:

With pyridine; at -20 ℃; for 2.5h;

DOI:10.1002/ejoc.200300791

Reference yield:

allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (628281-08-3) → allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside (727380-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / PPTS / methanol / 0.17 h / Heating

2: 90 percent / pyridine / 2.5 h / -20 °C

With pyridine; pyridinium p-toluenesulfonate; In methanol;

DOI:10.1002/ejoc.200300791

Reference yield:

allyl (6-O-acetyl-2,3-di-O-benzyl-β-D-glycopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside (727380-35-0) → Acetic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R,5R,6S)-6-allyloxy-5-amino-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200300791

upstream raw materials:

acetyl chloride

(2R,3R,4S,5R,6S)-6-((2R,3S,4R,5R,6S)-6-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol

allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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