1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose
• CAS No.: 109898-65-9
• Molecular Formula: C₃₀H₃₂N₆O₁₁
• Molecular Weight: 652.618

Synonyms:1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

Chemical Property:

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Technology Process of 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

There total 6 articles about 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose 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: 86.0%

acetic anhydride (108-24-7) + 1,6-Anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose (97783-75-0) → 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose (109898-65-9)

Guidance literature:

With pyridine; at 0 ℃; for 7h;

DOI:10.1016/0008-6215(86)80006-4

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) → 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose (109898-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) silver silicate, molecular sieves 4 Angstroem / 1.) toluol, 3 h, r.t., 2.) toluol

2: 97 percent / 0.1 M NaOMe / methanol / 8 h / Ambient temperature

3: 82 percent / O₂ / Pt (Adam's-katalysator) / H₂O; propan-1-ol / 6 h / 80 °C / NaHCO₃, pH 7.5

4: 62 percent / diethyl ether; methanol / Ambient temperature

5: 86 percent / pyridine / 7 h / 0 °C

With pyridine; silver silicate; 4 A molecular sieve; oxygen; sodium methylate; platinum(IV) oxide; In methanol; propan-1-ol; diethyl ether; water;

DOI:10.1016/0008-6215(86)80006-4

Reference yield:

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide (95451-93-7) → 1,6-anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose (109898-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) silver silicate, molecular sieves 4 Angstroem / 1.) toluol, 3 h, r.t., 2.) toluol

2: 97 percent / 0.1 M NaOMe / methanol / 8 h / Ambient temperature

3: 82 percent / O₂ / Pt (Adam's-katalysator) / H₂O; propan-1-ol / 6 h / 80 °C / NaHCO₃, pH 7.5

4: 62 percent / diethyl ether; methanol / Ambient temperature

5: 86 percent / pyridine / 7 h / 0 °C

With pyridine; silver silicate; 4 A molecular sieve; oxygen; sodium methylate; platinum(IV) oxide; In methanol; propan-1-ol; diethyl ether; water;

DOI:10.1016/0008-6215(86)80006-4

upstream raw materials:

acetic anhydride

1,6-Anhydro-2-azido-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

phenyldiazomethane

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

8-Methoxycarbonyloctyl-O--(1->4)-O-(2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-α-D-glucopyranosyl)-(1->3)4-acetamido-2-O-benzyl-4,6-didesoxy-α-D-galactopyranosid

2-Acetamido-1,6-di-O-acetyl-3-O-benzyl-4-O--2-desoxy-α-D-glucopyranose

2-Acetamido-1,6-di-O-acetyl-3-O-benzyl-4-O--2-desoxy-β-D-glucopyranose

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