1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate)

Base Information

• Chemical Name: 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate)
• CAS No.: 93041-22-6
• Molecular Formula: C₃₃H₃₃O₉P
• Molecular Weight: 604.593

Synonyms:1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate)

Chemical Property of 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate)

Chemical Property:

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Technology Process of 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate)

There total 2 articles about 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate) 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%

1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose (93041-21-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate) (93041-22-6)

Guidance literature:

With pyridine; at 25 ℃; for 1.5h;

DOI:10.1021/ja00337a034

Reference yield:

1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose (62255-44-1) → 1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate) (93041-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / pyridine, H₂ / 10percent Pd/C / acetic acid; methanol / 24 h

2: 86 percent / pyridine / 1.5 h / 25 °C

With pyridine; hydrogen; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1021/ja00337a034

Reference yield:

1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose 5-(diphenylphosphate) (93041-22-6) → Phosphoric acid (2R,3R,4S)-3,4-bis-benzyloxy-5-bromo-tetrahydro-furan-2-ylmethyl ester diphenyl ester

Guidance literature:

With hydrogen bromide; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ja00337a034

upstream raw materials:

1-O-acetyl-2,3-O-bis(phenylmethyl)-α-D-arabinofuranose

chlorophosphoric acid diphenyl ester

1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose

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