1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose
• CAS No.: 25258-08-6
• Molecular Formula: C₁₆H₂₀F₃NO₁₀
• Molecular Weight: 443.331

Synonyms:1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose

Chemical Property of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose

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Technology Process of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose

There total 2 articles about 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-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:

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose (667462-08-0) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-(trifluoroacetamido)-2-deoxy-β-D-glucopyranoside (7139-63-1) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose (25258-08-6)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 22h; Overall yield = 99 %; Overall yield = 10.9 g; Inert atmosphere;

DOI:10.1016/j.bmcl.2018.08.024

Reference yield:

→ 1,3,4,6-Tetra-O-acetyl-2-desoxy-2-trifluoracetamino-D-glucose (7139-63-1,25258-08-6,25258-09-7,25258-10-0,86900-32-5,137766-83-7)

Guidance literature:

1,3,4,6-Tetra-O-acetyl-2-amino-2-desoxy-β-D-glucose, Trifluoracetanhydrid in Pyridin;

DOI:10.1039/C1966000146a

Reference yield: 70.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose (25258-08-6) + acetyl chloride (75-36-5) → Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; chemoselective reaction;

DOI:10.1002/anie.200906055

upstream raw materials:

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose

acetic anhydride

Downstream raw materials:

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester

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